PREPARATION METHOD OF A GLYCOSIDE COMPOUND

Abstract

Preparation method of glycoside compounds is involved in the invention, with the advantages of short synthesis steps, high stereoselectivity and yield, simple production operation, low equipment requirements, environmental protection and suitability for industrial mass production.

Claims

1. A preparation method of a glycoside compound comprising the following two steps of reactions: (1) Acetyl-protected glucose (I) and alcohol compounds shown in formula (II) react under the catalysis of Lewis acid to obtain intermediates shown in formula (III); ##STR00107## (2) Remove acetyl protecting group from the intermediates shown in formula (III) in the presence of alkali to obtain glycoside compounds shown in formula (H.sup.+); ##STR00108## wherein in formulas II, III and IV, substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently selected from hydrogen, hydroxyl, substituted or unsubstituted C.sub.1˜C.sub.20 alkoxyl, substituted or unsubstituted C.sub.1˜C.sub.20 alkyl, substituted or unsubstituted C.sub.1˜C.sub.20 alkenyl, substituted or unsubstituted C.sub.1˜C.sub.20 alkynyl, substituted or unsubstituted aryl, heteroaryl, cycloalkyl, heterocyclyl, nitro or halogen; n is 4, 5, or 6.

2. The preparation method as described in claim 1, wherein the reaction in step (1) is carried out in the first organic solvent; and the first organic solvent as described is one or more of dichloromethane, chloroform, toluene, xylene, dimethylformamide, dioxane, methyl tert-butyl ether or tetrahydrofuran.

3. The preparation method as described in claim 1, wherein the Lewis acid in step (1) is one or more of tin tetrachloride, zinc chloride, aluminum trichloride and boron trifluoride complex, such as boron trifluoride diethyl ether complex, boron trifluoride butyl ether complex, boron trifluoride tetrahydrofuran complex, boron trifluoride acetonitrile complex or trimethylsilyl trifluoromethanesulfonate.

4. The preparation method as described in claim 1, wherein step (1) is carried out under the protection of inert gas nitrogen or argon.

5. The preparation method as described in claim 1, wherein the reaction temperature in step (1) is −15 to 60° C.

6. The preparation method as described in claim 5, wherein the reaction temperature in step (1) is −5 to 40° C.

7. The preparation method as described in claim 1, wherein the reaction in step (2) is carried out in the second organic solvent; the second organic solvent being one or more of methanol, ethanol, isobutanol or tert-butanol.

8. The preparation method described in claim 1, where the alkaline condition in step (2) refers to the existence of sodium hydroxide, potassium hydroxide or sodium salt of C.sub.1-C.sub.4 alkanol.

9. The preparation method as described in claim 8, wherein the alkaline condition as described in step (2) refers to that in the presence of sodium methoxide, sodium ethoxide or sodium tert-butoxide.

10. The preparation method as described in claim 1, wherein compound IV is selected from the following compounds: ##STR00109## ##STR00110## ##STR00111##

Description

Content of Invention

[0023] Preparation method of glycoside compounds is provided in the invention, which is featured by the following two steps of reactions:

[0024] (1) Acetyl-protected glucose (I) and alcohol compounds shown in formula (II) react under the catalysis of Lewis acid to obtain intermediates shown in formula (III).

##STR00008##

[0025] (2) Remove acetyl protecting group from the intermediates shown in formula (III) in the presence of alkali to obtain final glycoside compounds shown in formula (H.sup.+).

##STR00009##

[0026] In formulas II, III and IV, substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently selected from hydrogen, hydroxyl, substituted or unsubstituted C.sub.1-C.sub.20 alkoxyl, substituted or unsubstituted C.sub.1-C.sub.20 alkyl, substituted or unsubstituted C.sub.1-C.sub.20 alkenyl, substituted or unsubstituted C.sub.1-C.sub.20 alkynyl, substituted or unsubstituted aryl, heteroaryl, cycloalkyl, heterocyclyl, nitryl or halogen;

[0027] n is 4, 5, or 6.

[0028] Preferably, reaction in step (1) is conducted in the first organic solvent; the organic solvent is one or more of dichloromethane, chloroform, toluene, xylene, dimethylformamide, dioxane, methyl tert-butyl ether or tetrahydrofuran.

[0029] Preferably, Lewis acid in step (1) is one or more of tin tetrachloride, zinc chloride, aluminum trichloride and boron trifluoride complex, such as boron trifluoride diethyl ether complex, boron trifluoride butyl ether complex, boron trifluoride tetrahydrofuran complex, boron trifluoride acetonitrile complex or trimethylsilyl trifluoromethanesulfonate.

[0030] Preferably, step (1) is conducted under the protection of inert gas nitrogen or argon.

[0031] Preferably, reaction temperature in step (1) is −15˜60° C. More preferable reaction temperature is -5-40° C.

[0032] Preferably, reaction in step (2) is conducted in the second organic solvent; the second organic solvent is one or more of methanol, ethanol, isobutanol or tert-butanol.

[0033] Preferably, alkaline condition in step (2) refers to the presence of sodium hydroxide, potassium hydroxide or sodium salt of C.sub.1-C.sub.4 alkanol, more preferably the presence of sodium methoxide, sodium ethoxide or sodium tert-butoxide.

[0034] Specific operation steps of the invention are as follows: 1) In step (1), first, replace reaction flask with inert gas for 3 times, add the first solvent, and start stirring. Then, add β-D-glucose pentaacetate1,2,3,4,6-penta-O acetyl-β-D-glucopyranose I and alcohol II; control the temperature of the reaction flask to −15˜−60° C., more preferably −5˜−40° C. Add Lewis acid, and continue to stir for 2-24 h, preferably 4-12 h.

[0035] 2) After reaction in step (1), drop water into system to quench the reaction, separate liquid, wash the organic phase with Na.sub.2CO.sub.3 water solution, separate liquid again, and wash the organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III.

[0036] 3) In step (2), first, replace reaction flask with inert gas for 3 times, add the second solvent, and start stirring. Add intermediate III into reaction flask, control temperature at 25±5° C., add sodium hydroxide, potassium hydroxide or sodium salt of C.sub.1-C.sub.4 alkanol, more preferably sodium methoxide, sodium ethoxide or sodium tert-butoxide into reaction flask, and stir to react for 2 h.

[0037] 4) After reaction in step (2), conduct diatomite filtration, and collect filtrate after rinsing with the second solvent. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV.

[0038] According to preparation method of the invention, the synthesized glycoside compounds are featured by compound IV to be the following example but not limited to the following structure:

##STR00010## ##STR00011## ##STR00012##

[0039] Beneficial effects of this application are that: Compared with the existing synthesis technology of glycosides, the method of the invention is a direct condensation reaction of acetyl-protected glucosesthe monosaccharide protected by the full acetyl group and alcohols under the condition of Lewis acid catalysis to obtain the intermediate tetra-acetylated glycosides, and then alcoholysis of the intermediates under the alkaline condition to directly obtain the target glycoside compounds. The synthesis process has the advantages of short steps, high stereoselectivity and total yield, simple production and operation, low equipment requirements, environmental protection and suitability for industrial mass production. For a series of glycoside compounds constructed by this method, some compounds with specific structures have potential application prospects for cerebrovascular disease drugs.

[0040] Terminology:

[0041] “Alkyl” includes both branched and straight chains saturated aliphatic hydrocarbon groups, with a specified number of carbon atoms, generally 1 to about 12 carbon atoms. As used herein, term C.sub.1-C.sub.6 alkyl refers to an alkyl group with 1 to about 6 carbon atoms. When .sub.Co-Ca alkyl is used in combination with another group herein, taking (phenyl) C.sub.0-C.sub.4 alkyl as an example, the specified group, in this case, phenyl is directly bonded through a single covalent bond (C.sub.0) or connected through an alkyl chain with a specified number of carbon atoms (in this case, 1 to about 4 carbon atoms). Examples of alkyl include, but are not limited to: Methyl, ethyl, n-propyl, isopropyl, n-butyl, 3-methylbutyl, tert-butyl, n-pentyl, and sec-pentyl.

[0042] “Alkenyl” or “alkylene” refers to straight and branched hydrocarbon chains including one or more unsaturated carbon-carbon bonds, which can occur at any stable point along the chains. The alkenyl described herein generally have 2 to about 12 carbon atoms. Preferably, alkenyl is a low alkenyl, and those alkenyl groups have 2 to about 8 carbon atoms, such as C.sub.2-C.sub.8, C.sub.2-C.sub.6, and C.sub.2-C.sub.4 alkenyl. Examples of alkenyl include vinyl, allyl, and butenyl.

[0043] “Alkoxy” refers to an alkyl group as defined above with a specified number of carbon atoms connected by an oxygen bridge. Examples of alkoxy include, but are not limited to: Methoxy, ethoxy, 3-hexyloxy, and 3-methylpentyloxy.

[0044] Term “heterocyclic ring” refers to a 5- to 8-membered saturated ring, a partially unsaturated ring, or an aromatic ring containing 1 to about 4 heteroatoms selected from N, O and S with remaining ring atoms of carbon, or a 7- to 11-membered saturated ring, a partially unsaturated ring, or an aromatic heterocyclic ring system and a 10- to 15-membered tricyclic ring system, which contains at least 1 heteroatom selected from the polycyclic system of N, O and S, and each ring in the polycyclic system contains up to 4 heteroatoms independently selected from N, O and S. Unless otherwise specified, a heterocyclic ring can be connected to a group where it is substituted at any heteroatom and carbon atom and produces a stable structure. When specified, the heterocyclic ring described herein can be substituted on carbon or nitrogen atom as long as the obtained compound is stable. Optionally, nitrogen atoms in the heterocyclic ring can be quaternized. Preferably, the total number of heteroatoms in the heterocyclic group is no greater than 4 and the total number of S and O atoms in the heterocyclic group is no greater than 2, more preferably, no greater than 1. Examples of heterocyclic group include: Pyridyl, indolyl, pyrimidinyl, pyridizinyl, pyrazinyl, imidazolyl, oxazolyl, furyl, thiophenyl, thiazolyl, triazolyl, tetrazolyl, isoxazolyl, quinolyl, pyrrolyl, pyrazolyl, benz[b]thiophenyl, isoquinolyl, quinazolinyl, quinoxalinyl, thienyl, isoindolyl, dihydrogen indole, 5,6,7,8- tetrahydroisoquinoline, pyridyl, pyrimidinyl, furyl, thienyl, pyrrolyl, pyrazolyl, pyrrolidyl, morpholinyl, piperazinyl, piperidinyl, and pyrrolidyl.

[0045] “Aryl” or “heteroaryl” refers to a stable 5- or 6-membered monocyclic or polycyclic ring containing 1 to 4 heteroatoms, or preferably 1 to 3 heteroatoms selected from N, O and S, with remaining ring atoms of carbon. When the total number of S and O atoms in heteroaryl exceeds 1, these heteroatoms are not adjacent to each other. Preferably, the total number of S and O atoms in heteroaryl is no greater than 2. Especially, the total number of S and O atoms in heteroaryl is no greater than 1. Optionally, the nitrogen atoms in the heterocyclic ring can be quaternized. When specified, these heteroaryl groups can also be substituted with carbon or non-carbon atoms or groups. Such substitution may include fusion with a 5- to 7-membered saturated cyclic groups optionally containing 1 or 2 heteroatoms independently selected from N, O and S, thus forming, for example, [1,3] dioxazole [4,5-c] pyridyl. Examples of heteroaryl include, but are not limited to: Pyridyl, indolyl, pyrimidinyl, pyridazinyl, pyrazinyl, imidazolyl, oxazolyl, furyl, phenylthio, thiazolyl, triazolyl, tetrazolyl, isoxazolyl, quinolyl, pyrrolyl, pyrazolyl, benz[b]thiophenyl, isoquinolyl, quinazolyl, quinoxalinyl, thienyl, isoindolyl, and 5,6,7,8-tetrahydroisoquinoline.

Specific Implementation

[0046] Next, the invention will be further described in detail in combination with specific implementation. Examples given are only to illustrate the invention, but not to limit the scope of it.

EXAMPLE 1

Synthesis of 1-[4-(2-methoxyphenyl) butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-1

[0047] ##STR00013##

[0048] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(2-methoxyphenyl)butan- 1 -ol II-1 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride tetrahydrofuran complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench the reaction, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-1, with a yield of 30%. H NMR (400 MHz, CDCl.sub.3): δ 6.32 (d, J=2 .2 Hz, 2H), 6.29 (t, J=2 .2 Hz, 1H), 5.20 (t, J=9.5 Hz, 1H), 5.08 (t, J=9.7 Hz, 1H), 4.98 (dd, J=9.6, 8.0 Hz, 1H), 4.48 (d , J=8.0 Hz, 1H), 4.26 (dd, J=12.3, 4.7 Hz, 1H), 4.13 (dd, J=12.3, 2.3 Hz, 1H), 3.89 (d, J=9.5 Hz, 1H), 3.78 (s, 6H), 3.68 (dd, J=9.9, 2.2 Hz, 1H), 3.49 (d, J=9.4 Hz, 1H), 2.55 (t, J=6.6 Hz, 2H), 2.08 (s, 3H), 2.05-1.97 (m, 9H), 1.63 (dd, J=11.5, 4.3 Hz, 4H). LRMS(ESI): [M+Na].sup.+533.5.

Synthesis of 1-(2-methoxy)phenylbutyl-β-D-glucopyranoside IV-1

[0049] ##STR00014##

[0050] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-1 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction bottle, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-1, with a yield of 89%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.17-7.06 (m, 2H), 6.88 (d, J=8.0 Hz, 1H), 6.82 (td, J=7.4, 0.9 Hz, 1H), 4.23 (d, J=7.8 Hz, 1H), 3.91 (m, 1H), 3.85 (dd, J=11.9, 2.0 Hz, 1H), 3.80 (s, 3H), 3.66 (dd, J=11.9, 5.3 Hz, 1H), 3.55 (m, 1H), 3.37-3.21 (m, 3H), 3.19-3.12 (m, 1H), 2.61 (t, J=7.0 Hz, 2H), 1.64 (m, 4H). LRMS(ESI): [M+Na].sup.+365.1; HRMS(ESI): m/z Calcd for C.sub.17H.sub.27O.sub.7.sup.+[M+H].sup.+:calculated value is C.sub.17H.sub.27O.sub.7.sup.+343.1751, Found: 343.1748.

EXAMPLE 2

Synthesis of 1-[4(3-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-2

[0051] ##STR00015##

[0052] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(3-methoxyphenyl)butan-1-ol II-2 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain final product III-2, with a yield of 26%. .sup.1H NMR (300 MHz, CDCl.sub.3): δ 7.19 (t, J=8.1 Hz, 1H), 6.81-6.65 (m, 3H), 5.28-4.88 (m, 3H), 4.48 (d, J=8.0 Hz, 1H), 4.32-4.06 (m, 2H), 3.88 (m, 1H), 3.80 (s, 3H), 3.68 (d, J=8.2 Hz, 1H), 3.51 (m, 1H), 2.59 (m, 2H), 2.03 (m, 12H), 1.64 (m, 4H). LRMS(ESI): [M+Na].sup.+533.5.

Synthesis of 1-(3-methoxy)phenylbutyl-β-D-glucopyranoside IV-2

[0053] ##STR00016##

[0054] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-2 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-2, with a yield of 92%. .sup.i H NMR (400 MHz, CD.sub.3OD): δ 7.15 (t, J=7.8 Hz, 1H), 6.79-6.67 (m, 3H), 4.24 (d, J=7.8 Hz, 1H), 3.92 (dt, J=9.4, 6.4 Hz, 1H), 3.85 (dd, J=11.9, 1.8 Hz, 1H), 3.76 (s, 3H), 3.66 (dd, J=11.9, 5.2 Hz, 1H), 3.60-3.51 (m, 1H), 3.39-3.21 (m, 3H), 3.19-3.12 (m, 1H), 2.60 (t, J=7.3 Hz, 2H), 1.78-1.56 (m, 4H). LRMS(ESI): [M+Na].sup.+365.1; HRMS(ESI): m/z Calcd for C.sub.17H.sub.30O.sub.7N.sup.+[M+NH.sub.4].sup.+: calculated value C.sub.17H.sub.30O.sub.7N.sup.+360.2017, found: 360.2016.

EXAMPLE 3

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0055] ##STR00017##

[0056] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring.

[0057] Then, add β-D-glucose pentaacetate I and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-3, with a yield of 37%. .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.0 (d, J=8.6 Hz, 2H), 6.82 (t, J=5.7 Hz, 2H), 5.20 (t, J=9.5 Hz, 1H), 5.08 (t, J=9.7 Hz, 1H), 4.98 (t, J=9.6, 8.0 Hz, 1H), 4.48 (d, J=8.0 Hz, 1H), 4.26 (dd, J=12.3, 4.7 Hz, 1H), 4.16-4.07 (m, 1H), 3.89 (dd, J=5.8, 3.7 Hz, 1H), 3.78 (s, 3H), 3.68 (m, J=9.9, 4.6, 2.4Hz, 1H), 3.49 (dt, J=9.4, 6.1 Hz, 1H), 2.55 (t, J=6.6Hz, 2H), 2.08 (s, 3H), 2.05-1.96 (m, 9H), 1.68-1.52 (m, 4H). LRMS(ESI): [M+Na].sup.+533.2.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0058] ##STR00018##

[0059] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-3 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 91%. .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 7.10 (d, J=8.5 Hz, 2H), 6.83 (d, J=8.5Hz, 2H), 5.10-4.78 (m, 3H), 4.45 (t, J=5.9 Hz, 1H), 4.09 (d, J=7.8 Hz, 1H), 3.77 (m, J=12.5, 6.4 Hz, 1H), 3.71 (s, 3H), 3.65 (dd, J=10.8, 6.0 Hz, 1H), 3.49-3.37 (m, 2H), 3.17-2.98 (m, 3H), 2.92 (td, J=8.3, 5.1 Hz, 1H), 2.55-2.5 (m, 2H), 1.69-1.41 (m, 4H). LRMS(ESI): [M+Na].sup.+365.0; HRMS(ESI): m/z Calcd for C.sub.17H.sub.26O.sub.7Na.sup.+[M+Na].sup.+: 365.1571, found: 365.1569.

EXAMPLE 4

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0060] ##STR00019##

[0061] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-3, with a yield of 38%. .sup.1H NMR and LRMS are consistent with Example 3.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0062] ##STR00020##

[0063] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-3 (1.0 eq) into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 89%. .sup.1H NMR and LRMS are consistent with Example 3.

EXAMPLE 5

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0064] ##STR00021##

[0065] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride tetrahydrofuran complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-3, with a yield of 34%. .sup.1H NMR and LRMS are consistent with Example 3.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0066] ##STR00022##

[0067] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-3 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 85%. .sup.1H NMR and LRMS are consistent with Example 3.

EXAMPLE 6

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0068] ##STR00023##

[0069] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride tetrahydrofuran complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-3, with a yield of 32%. .sup.1H NMR and LRMS are consistent with Example 3.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0070] ##STR00024##

[0071] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-3 (1.0 eq) into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 84%. .sup.1H NMR and LRMS are consistent with Example 3.

EXAMPLE 7

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0072] ##STR00025##

[0073] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl ether complex , and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-3, with a yield of 31%. .sup.1H NMR and LRMS are consistent with Example 3.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0074] ##STR00026##

[0075] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-3 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 91%. .sup.1H NMR and LRMS are consistent with Example 3.

EXAMPLE 8

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0076] ##STR00027##

[0077] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl ether complex , and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-3, with a yield of 33%. i H NMR and LRMS are consistent with Example 3.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0078] ##STR00028##

[0079] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring.

[0080] Add intermediate III-3 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 95%. .sup.1H NMR and LRMS are consistent with Example 3.

EXAMPLE 9

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0081] ##STR00029##

[0082] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride acetonitrile complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-3, with a yield of 36%. .sup.1H NMR and LRMS are consistent with Example 3.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0083] ##STR00030##

[0084] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-3 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 88%. .sup.1H NMR and LRMS are consistent with Example 3.

EXAMPLE 10

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0085] ##STR00031##

[0086] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride acetonitrile complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-3, with a yield of 30%. .sup.1H NMR and LRMS are consistent with Example 3.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0087] ##STR00032##

[0088] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-3 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 86%. .sup.1H NMR and LRMS are consistent with Example 3.

EXAMPLE 11

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0089] ##STR00033##

[0090] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., drop trimethylsilyl trifluoromethanesulfonate, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-3, with a yield of 28%. H NMR and LRMS are consistent with Example 3.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0091] ##STR00034##

[0092] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-3 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 84%. .sup.1H NMR and LRMS are consistent with Example 3.

EXAMPLE 12

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0093] ##STR00035##

[0094] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., drop trimethylsilyl trifluoromethanesulfonate, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-3, with a yield of 26%. .sup.1H NMR and LRMS are consistent with Example 3.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0095] ##STR00036##

[0096] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-3 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 89%. .sup.1H NMR and LRMS are consistent with Example 3.

EXAMPLE 13

Synthesis of 1-[4(4-methoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-3

[0097] ##STR00037##

[0098] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I, tin tetrachloride and 4-(4-methoxyphenyl)butan-1-ol II-3 in turn. Cool reaction flask to 0±5° C., stir to react for 12 h. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-3, with a yield of 25%. .sup.1H NMR and LRMS are consistent with Example 3.

Synthesis of 1-(4-methoxy)phenylbutyl-β-D-glucopyranoside IV-3

[0099] ##STR00038##

[0100] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-3 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-3, with a yield of 92%. .sup.1H NMR and LRMS are consistent with Example 3.

EXAMPLE 14

Synthesis of 1-[4(3,4-dimethoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-4

[0101] ##STR00039##

[0102] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(3,4-dimethoxyphenyl)butan-1-ol II-4 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-4, with a yield of 33%. .sup.1H NMR (300 MHz, CDCl.sub.3): δ 6.82-6.59 (m, 3H), 5.27-4.83 (m, 3H), 4.46 (d, J=7.9 Hz, 1H), 4.32-3.99 (m, 2H),n 3.83 (m, 7H), 3.74-3.35 (m, 2H), 2.53 (m, 2H), 1.99 (m, 12H), 1.59 (m, 4H). LRMS(ESI): [M+Na].sup.+563.5.

Synthesis of 1-(3,4-dimethoxy)phenylbutyl-β-D-glucopyranoside IV-4

[0103] ##STR00040##

[0104] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-4 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-4, with a yield of 85%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 6.84 (d, J=8.2 Hz, 1H), 6.79 (d, J=1.9 Hz, 1H), 6.72 (dd, J=8.1, 1.9 Hz, 1H), 4.24 (d, J=7.8 Hz, 1H), 3.98-3.88 (m, 1H), 3.86 (dd, J=11.9, 1.9 Hz, 1H), 3.81 (s, 3H), 3.79 (s, 1H), 3.66 (dd, J=11.9, 5.3 Hz, 1H), 3.61-3.51 (m, 1H), 3.38-3.21 (m, 3H), 3.20-3.12 (m, 1H), 2.58 (t, J=7.2 Hz, 2H), 1.75-1.56 (m, 4H). LRMS(ESI): [M+Na].sup.+395.1; HRMS(ESI): m/z Calcd for C.sub.18H.sub.32O.sub.8N.sup.+[M+NH.sub.4].sup.+: 390.2122, Found: 390.2118.

EXAMPLE 15

Synthesis of 1-[4(3,5-dimethoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-5

[0105] ##STR00041##

[0106] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(3,5-dimethoxyphenyl)butan-1-ol II-5 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride acetonitrile complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-5, with a yield of 26%. .sup.1H NMR (400 MHz, CDCl.sub.3): δ 6.34-6.28 (m, 3H), 5.20 (t, J=9.5 Hz, 1H), 5.08 (t, J=9.7 Hz, 1H), 4.98 (dd, J=9.6, 8.0 Hz, 1H), 4.48 (d, J=8.0 Hz, 1H), 4.26 (dd, J=12.3, 4.7 Hz, 1H), 4.13 (dd, J=12.3, 2.3 Hz, 1H), 3.89 (d, J=9.5 Hz, 1H), 3.78 (s, 6H), 3.68 (dd, J=9.9, 2.2 Hz, 1H), 3.49 (d, J=9.4 Hz, 1H), 2.55 (t, J=6.6 Hz, 2H), 2.10-2.07 (s, 3H), 2.03 (s, 3H), 2.00 (m, 6H), 1.63 (dd, J=11.5, 4.3 Hz, 4H). LRMS(ESI): [M+Na].sup.+563.5.

Synthesis of 1-(3,5-dimethoxy)phenylbutyl-β-D-glucopyranoside IV-5

[0107] ##STR00042##

[0108] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-5 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-5, with a yield of 85%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 6.35 (d, J=2.2 Hz, 2H), 6.28 (t, J=2.2 Hz, 1H), 4.24 (d, J=7.8 Hz, 1H), 3.96-3.91 (m, 1H), 3.85 (dd, J=11.8, 1.7 Hz, 1H), 3.74 (s, 6H), 3.66 (dd, J=11.9, 5.2 Hz, 1H), 3.58-3.53 (m, 1H), 3.38-3.21 (m, 3H), 3.19-3.11 (m, 1H), 2.57 (t, J=7.3 Hz, 2H), 1.75-1.58 (m, 4H). LRMS(ESI): [M+Na].sup.+395.1; HRMS(ESI): m/z Calcd for C.sub.18H.sub.32O.sub.8N.sup.+: 390.2122, Found: 390.2122.

EXAMPLE 16

Synthesis of 1-[4(3,4,5-triethoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-6

[0109] ##STR00043##

[0110] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(3,4,5-trimethoxyphenyl)butan-1-ol II-6 in turn. Cool reaction flask to 0±5° C., drop trifluoromethanesulfonic acid trimethylsilyl, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatographic purification after organic phase concentration, and obtain compound III-6, with a yield of 24%. LRMS(ESI): [M+Na].sup.+593.5.

Synthesis of 1-(3,4,5-trimethoxy)phenylbutyl-β-D-glucopyranoside IV-6

[0111] ##STR00044##

[0112] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-6 (1.0 eq) into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-6, with a yield of 88%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 6.49 (s, 2H), 4.24 (d, J=7.8 Hz, 1H), 3.97-3.83 (m, 2H), 3.81 (s, 6H), 3.72 (s, 3H), 3.69-3.52 (m, 2H), 3.37-3.21 (m, 3H), 3.20-3.13 (m, 1H), 2.59 (t, J=7.3 Hz, 2H), 1.79-1.55 (m, 4H). LRMS(ESI): [M+Na].sup.+425.1; HRMS(ESI): m/z Calcd for C.sub.19H.sub.34O.sub.9N+[M+NH.sub.4].sup.+: 420.2228, Found: 420.2226.

EXAMPLE 17

Synthesis of 1-[5-(4-methoxyphenypamyl]-2,3,4,6-O-tetraacetyl-β-D- glucopyranoside III-7

[0113] ##STR00045##

[0114] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 5-(4-methoxyphenyl)pentan-1-ol II-7 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl etherate, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-7, with a yield of 22%. .sup.1H NMR (300 MHz, CDCl.sub.3): δ 7.08 (d, J=6.9 Hz, 2H), 6.82 (d, J=6.8 Hz, 2H), 5.69 (d, J=4.2 Hz, 1H), 5.19 (m, 1H), 4.91 (d, J=9.3 Hz, 1H), 4.30 (m, 1H), 4.20 (m, 2H), 3.96 (m, 1H), 3.79 (s, 3H), 3.46 (t, J=5.7 Hz, 2H), 2.55 (t, J=7.0 Hz, 2H), 2.09 (m, 9H), 1.71 (s, 3H), 1.66-1.48 (m, 4H), 1.36 (d, J=6.7 Hz, 2H). LRMS(ESI): [M+Na].sup.+547.5.

Synthesis of 1-(4-methoxy)phenylamyl-β-D-glucopyranoside IV-7

[0115] ##STR00046##

[0116] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-7 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-7, with a yield of 95%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.07 (d, J=8.8 Hz, 2H), 6.80 (d, J=8.8Hz, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.93-3.82 (m, 2H), 3.75 (s, 3H), 3.66 (dd, J=11.9, 5.3 Hz, 1H), 3.52 (dt, J=9.5, 6.7 Hz, 1H), 3.38-3.22 (m, 3H), 3.20-3.12 (m, 1H), 2.54 (t, J=7.6 Hz, 2H), 1.68-1.61 (m, 4H), 1.47-1.31 (m, 2H). LRMS(ESI): [M+Na].sup.+375.1; HRMS(ESI): m/z Calcd for Cl.sub.18H.sub.29O.sub.7.sup.+[M+H].sup.+: 357.1908, found: 357.1906.

EXAMPLE 18

Synthesis of 1-[6-(4-methoxyphenyphexyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-8

[0117] ##STR00047##

[0118] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I, tin tetrachloride and 6-(4-methoxyphenyl)hexan-1-ol II-8 in turn. Cool reaction flask to 0±5° C., stir to react for 10 h. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography after organic phase concentration, and obtain compound III-8, with a yield of 18%. .sup.1H NMR (400 MHz, CDCl.sub.3): δ 7.08 (d, J=8.6 Hz, 2H), 6.83 (t, J=5.7 Hz, 2H), 5.20 (t, J=9.5 Hz, 1H), 5.08 (t, J=9.7 Hz, 1H), 4.98 (dd, J=9.6, 8.0 Hz, 1H), 4.48 (d, J=8.0 Hz, 1H), 4.26 (dd, J=12.3, 4.7 Hz, 1H), 4.12 (m, 1H), 3.86 (dt, J=9.6, 6.3 Hz, 1H), 3.79 (s, 3H), 3.68 (ddd, J=9.9, 4.6, 2.4 Hz, 1H), 3.46 (dt, J=9.5, 6.8 Hz, 1H), 2.58-2.49 (m, 2H), 2.08 (s, 3H), 2.02 (m, 9H), 1.62-1.49 (m, 4H), 1.36-1.28 (m, 4H). LRMS(ESI): [M+Na].sup.+561.5.

Synthesis of 1-(4-methoxy)phenylhexyl-β-D-glucopyranoside IV-8

[0119] ##STR00048##

[0120] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-8 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-8, with a yield of 84%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.06 (d, J=8.6 Hz, 2H), 6.84-6.80 (d, J=8.6Hz, 2H), 4.23 (d, J=7.8Hz, 1H), 3.93-3.82 (m, 2H), 3.75 (s, 3H), 3.66 (dd, J=11.9, 5.2 Hz, 1H), 3.52 (dt, J=9.5, 6.7 Hz, 1H), 3.38-3.21 (m, 3H), 3.20-3.11 (m, 1H), 2.53 (t, J=7.6 Hz, 2H), 1.68-1.50 (m, 4H), 1.47-1 .25 (m, 4H). LRMS(ESI): [M+Na].sup.+393.1; HRMS(ESI): m/z Calcd for C.sub.19H.sub.34O.sub.7N.sup.+[M+NH.sub.4].sup.+: 388.2330, found: 388.2327.

EXAMPLE 19

Synthesis of 1-[4(4-fluorophenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-9

[0121] ##STR00049##

[0122] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-fluorophenyl)butan-1-ol II-9 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-9, with a yield of 22%. LRMS(ESI): [M+Na].sup.+521.5.

Synthesis of 1-(4-fluoro)phenylbutyl-β-D-glucopyranoside IV-9

[0123] ##STR00050##

[0124] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-9 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-9, with a yield of 93%. i H NMR (400 MHz, CD.sub.3OD): δ 7.18 (dd, J=8.5, 5.6 Hz, 2H), 7.00-6.91 (m, 2H), 4.24 (d, J=7.8 Hz, 1H), 3.92 (dt, J=9.6, 6.3 Hz, 1H), 3.87-3.82 (m, 1H), 3.66 (dd, J=11.8, 5.2 Hz, 1H), 3.56 (dt, J=9.5, 6.3 Hz, 1H), 3.37 3.22 (m, 3H), 3.20-3.11 (m, 1H), 2.62 (t, J=7.3 Hz, 2H), 1.78-1.54 (m, 4H). LRMS(ESI): [M+COOH].sup.−375.0; HRMS(ESI): m/z Calcd for C.sub.16H.sub.23O.sub.6FCl.sup.−[M+Cl].sup.−: 365.1173, Found: 365.1173.

EXAMPLE 20

Synthesis of 1-[4(4-bromophenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-10

[0125] ##STR00051##

[0126] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-bromophenyl)butan-1-ol II-10 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-10, with a yield of 18%. LRMS(ESI): [M+Na].sup.+582.4.

Synthesis of 1-(4-bromo)phenylbutyl-β-D-glucopyranoside IV-10

[0127] ##STR00052##

[0128] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-10 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-10, with a yield of 83%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.38 (d, J=8.3 Hz, 2H), 7.12 (d, J=8.3 Hz, 2H), 4.24 (d, J=7.8 Hz, 1H), 3.92 (dt, J=9.5, 6.4 Hz, 1H), 3.85 (dd, J=11.9, 1.6 Hz, 1H), 3.66 (dd, J=11.8, 5.2 Hz, 1H), 3.56 (dt, J=9.6, 6.3 Hz, 1H), 3.31 (m, 3H), 3.19-3.11 (m, 1H), 2.61 (t, J=7.4 Hz, 2H), 1.77-1.55 (m, 4H). LRMS(ESI): [M+Na].sup.+414.9; HRMS(ESI): m/z Calcd for C.sub.16H.sub.23O.sub.6BrNa.sup.+[M+Na].sup.+: 413.0570, Found: 413.0568.

EXAMPLE 21

Synthesis of 1-[4(4-nitrophenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-11

[0129] ##STR00053##

[0130] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-nitrophenyl)butan-1-ol II-11 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatographic purification after organic phase concentration, and obtain compound III-11, with a yield of 27%. LRMS(ESI): [M+Na].sup.+548.5.

Synthesis of 1-(4-nitro)phenylbutyl-β-D-glucopyranoside IV-11

[0131] ##STR00054##

[0132] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-11 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-11, with a yield of 89%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 8.14 (d, J=8.7 Hz, 2H), 7.45 (d, J=8.7 Hz, 2H), 4.25 (d, J=7.8 Hz, 1H), 4.00-3.82 (m, 2H), 3.70-3.50 (m, 2H), 3.37-3.22 (m, 3H), 3.21-3.12 (m, 1H), 2.78 (t, J=7.6 Hz, 2H), 1.85-1.57 (m, 4H). LRMS(ESI): [M+Na].sup.+380.0; HRMS(ESI): m/z Calcd for C.sub.16H.sub.23O.sub.8NNa.sup.+[M+Na].sup.+: 380.1327, Found: 380.1314.

EXAMPLE 22

Synthesis of 1-[4(4-hydroxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-12

[0133] ##STR00055##

[0134] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-hydroxybutyl)phenol II-12 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-12, with a yield of 22%. LRMS(ESI): [M+Na].sup.+519.2.

Synthesis of 1-(4-hydroxyl)phenylbutyl-β-D-glucopyranoside IV-12

[0135] ##STR00056##

[0136] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-12 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-12, with a yield of 79%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 6.99 (d, J=8.5 Hz, 2H), 6.70-6.63 (m, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.96-3.82 (m, 2H), 3.66 (dd, J=11.9, 5.2 Hz, 1H), 3.54 (dt, J=9.5, 6.1 Hz, 1H), 3.38-3.21 (m, 3H), 3.16 (dd, 1H), 2.53 (t, J=7.0 Hz, 2H), 1.70-1.56 (m, 4H). LRMS(ESI): [M+Na].sup.+351.1; HRMS(ESI): m/z Calcd for C.sub.16H.sub.28O.sub.7N.sup.+[M+NH.sub.4].sup.+: 346.1860, Found: 346.1857.

EXAMPLE 23

Synthesis of 1-[4(4-hydroxyl-3-methoxyphenyl)butyl]-2,3,4,6-O- tetraacetyl-β-D-glucopyranoside III-13

[0137] ##STR00057##

[0138] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-hydroxybutyl)-2-methoxyphenol II-13 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatographic purification after organic phase concentration, and obtain compound III-13, with a yield of 19%. LRMS(ESI): [M-H] - 525.2.

Synthesis of 1-(4-hydroxyl-3-methoxy)phenylbutyl-β-D-glucopyranoside IV-13

[0139] ##STR00058##

[0140] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-13 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-13, with a yield of 80%. .sup.1H NMR (400 MHz, CDCl.sub.3): δ 6.83 (d, J=7.6Hz, 1H), 6.70-6.64 (m, 2H), 6.26 (br, 1H), 4.83 (br, 8H), 4.00 (s, 1H), 3.88 (s, 3H), 3.74 (t, J=6.4 Hz, 2H), 3.55 (s, 2H), 2.58 (t, J=7.2 Hz, 2H), 1.69-1.62 (m, 4H). LRMS(ESI): [M+Na].sup.+381.2.

EXAMPLE 24

Synthesis of 1-[4(3,4-methylenedioxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-14

[0141] ##STR00059##

[0142] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(benzo[d][1,3]dioxol-5-yl)butan-1-ol II-14 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride tetrahydrofuran complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-14, with a yield of 27%. LRMS(ESI): [M+Na].sup.+547.5.

Synthesis of 1-(3,4-methylenedioxy)phenylbutyl-β-D-glucopyranoside IV-14

[0143] ##STR00060##

[0144] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-14 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-14, with a yield of 82%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 6.71-6.67 (m, 2H), 6.65-6.61 (m, 1H), 5.87 (s, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.95-3.88 (m, 1H), 3.85 (m, 1H), 3.66 (dd, J=11.8, 5.2 Hz, 1H), 3.60-3.48 (m, 1H), 3.38-3.20 (m, 3H), 3.19-3.12 (m, 1H), 2.55 (t, J=7.1 Hz, 2H), 1.73-1.53 (m, 4H). LRMS(ESI): [M+Na].sup.+379.0; HRMS(ESI): m/z Calcd for C.sub.17H.sub.24O.sub.8Na.sup.+[M+Na].sup.+: 379.1374, Found: 379.1362.

EXAMPLE 25

Synthesis of 1-[4(4-ethoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-15

[0145] ##STR00061##

[0146] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring.

[0147] Then, add β-D-glucose pentaacetate I and 4-(4-ethoxyphenyl)butan-1-ol II-15 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride acetonitrile complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-15, with a yield of 26%. LRMS(ESI): [M+Na].sup.+547.2.

Synthesis of 1-(4-ethoxy)phenylbutyl-β-D-glucopyranoside IV-15

[0148] ##STR00062##

[0149] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-15 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-15, with a yield of 92%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.10 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.6 Hz, 2H), 4.27 (d, J=7.8 Hz, 1H), 4.02 (q, J=7.0 Hz, 2H), 3.98-3.92 (m, 1H), 3.89 (dd, J=11.8, 1.6 Hz, 1H), 3.69 (dd, J=11.8, 5.2 Hz, 1H), 3.58 (dt, J=9.5, 6.2 Hz, 1H), 3.41-3.29 (m, 3H), 3.23-3.13 (m, 1H), 2.59 (t, J=7.1 Hz, 2H), 1.78-1.56 (m, 4H), 1.39 (t, J=7.0 Hz, 3H). LRMS(ESI): [M+Na].sup.+379.1.

EXAMPLE 26

Synthesis of 1-[4(4-n-propoxyphenyl)butyl]-2,3,4,6-O- tetraacetyl-β-D-glucopyranoside III-16

[0150] ##STR00063##

[0151] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-n-propoxyphenyl)butan-1-ol II-16 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride acetonitrile complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-16, with a yield of 33%. LRMS(ESI): [M+Na].sup.+561.5.

Synthesis of 1-(4-propoxy)phenylbutyl-β-D-glucopyranoside IV-16

[0152] ##STR00064##

[0153] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-16 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-16, with a yield of 94%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.07 (d, J=8.5 Hz, 2H), 6.79 (d, J=8.6Hz, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.96-3.80 (m, 4H), 3.66 (dd, J=11.9, 5.2 Hz, 1H), 3.59-3.49 (m, 1H), 3.38-3.21 (m, 3H), 3.20-3.11 (m, 1H), 2.56 (t, J=7. 1Hz, 2H), 1.75 (m, 2H), 1.70-1.57 (m, 4H), 1.02 (t, J=7.4 Hz, 3H). LRMS(ESI): [M+Na].sup.+393.1; HRMS(ESI): m/z Calcd for C.sub.19H.sub.30O.sub.7Na.sup.+[M+Na].sup.+: 393.1884, Found: 393.1880.

EXAMPLE 27

Synthesis of 1-[4(4-isopropoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-17

[0154] ##STR00065##

[0155] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-isopropoxyphenyl)butan-1-ol II-17 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride acetonitrile complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-17, with a yield of 35%. LRMS(ESI): [M+Na].sup.+561.2.

Synthesis of 1-(4-isopropoxy)phenylbutyl-β-D-glucopyranoside IV-17

[0156] ##STR00066##

[0157] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-17 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-17, with a yield of 88%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.07 (d, J=8.6 Hz, 2H), 6.89-6.70 (m, 2H), 4.52 (dt, J=12.1, 6.1 Hz, 1H), 4.23 (d, J=7.8 Hz, 1H), 3.95-3.88 (m, 1H), 3.85 (dd, J=11.9, 1.9 Hz, 1H), 3.66 (dd, J=11.8, 5.3 Hz, 1H), 3.62-3.51 (m, 1H), 3.36-3.33 (m, 1H), 3.28-3.20 (m, 2H), 3.17 (dd, J=15.1, 7.2 Hz, 1H), 2.56 (t, J=7.1 Hz, 2H), 1.75-1.54 (m, 4H), 1.27 (d, J=6.0 Hz, 6H). LRMS(ESI): [M+Na].sup.+393.0; HRMS(ESI): m/z Calcd for C.sub.19H.sub.30O.sub.7Na.sup.+[M+Na].sup.+: 393.1884, Found: 393.1880.

EXAMPLE 28

Synthesis of 1-[4(4-allyloxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-18

[0158] ##STR00067##

[0159] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(allyloxy)phenyl)butan-1-ol II-18 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl etherate, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-18, with a yield of 18%. LRMS(ESI): [M+Na].sup.+559.5.

Synthesis of 1-(4-allyloxy)phenylbutyl-β-D-glucopyranoside IV-18

[0160] ##STR00068##

[0161] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-18 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-18, with a yield of 81%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.08 (d, J=8.6 Hz, 2H), 6.82 (d, J=8.6 Hz, 2H), 6.12-5.96 (m, 1H), 5.37 (dd, J=17.3, 1.6 Hz, 1H), 5.22 (dd, J=10.6, 1.4 Hz, 1H), 4.55-4.44 (m, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.97-3.80 (m, 2H), 3.66 (dd, J=11.9, 5.2 Hz, 1H), 3.60-3.50 (m, 1H), 3.38-3.21 (m, 3H), 3.20-3.12 (m, 1H), 2.56 (t, J=7.1 Hz, 2H), 1.73-1.55 (m, 4H). LRMS(ESI): [M+Na].sup.+391.0; HRMS(ESI): m/z Calcd for C.sub.19H.sub.28O.sub.7Na.sup.+[M+Na].sup.+: 391.1727, Found: 391.1726.

EXAMPLE 29

Synthesis of 1-[4(4-cyclopropylmethoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-19

[0162] ##STR00069##

[0163] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(cyclopropylmethoxy)phenyl)butan-1-ol II-19 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-19, with a yield of 18%. LRMS(ESI): [M+Na].sup.+573.2.

Synthesis of 1-(4-cyclopropylmethoxy)phenylbutyl-β-D-glucopyranoside IV-19

[0164] ##STR00070##

[0165] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-19 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-19, with a yield of 78%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.07 (d, J=8.6 Hz, 2H), 6.79 (d, J=8.6 Hz, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.91 (m, 1H), 3.88-3.82 (m, 1H), 3.77 (d, J=6.8 Hz, 2H), 3.67 (dd, J=12.0, 5.3 Hz, 1H), 3.55 (m, 1H), 3.33-3.17 (m, 4H), 2.56 (t, J=7.1 Hz, 2H), 1.76-1.54 (m, 4H), 1.27-1.16 (m, 1H), 0.59 (dd, J=8.1, 1.4 Hz, 2H), 0.38-0.24 (m, 2H). LRMS(ESI): [M+Na].sup.+405.0; HRMS(ESI): m/z Calcd for C.sub.20H.sub.30O.sub.7Na.sup.+[M+Na].sup.+: 405.1884, Found: 405.1883.

EXAMPLE 30

Synthesis of 1-[4(4-cyclobutylmethoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-20

[0166] ##STR00071##

[0167] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(cyclobutylmethoxy)phenyl)butan-1-ol II-20 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-20, with a yield of 25%. LRMS(ESI): [M+Na].sup.+587.6.

Synthesis of 1-(4-cyclobutylmethoxy)phenylbutyl-β-D-glucopyranoside IV-20

[0168] ##STR00072##

[0169] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-20 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-20, with a yield of 77%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.10 (d, J=8.5 Hz, 2H), 6.83 (d, J=8.5 Hz, 2H), 4.27 (d, J=7.8 Hz, 1H), 3.99-3.85 (m, 4H), 3.69 (dd, J=11.8, 5.2 Hz, 1H), 3.58 (dt, J=9.4, 6.2 Hz, 1H), 3.41-3.24 (m, 3H), 3.19 (t, J=8.4 Hz, 1H), 2.85-2.71 (m, 1H), 2.59 (t, J=7.1 Hz, 2H), 2.24-2.08 (m, 2H), 2.08-1.85 (m, 4H), 1.70 (m, 4H). LRMS(ESI): [M+Na].sup.+419.2.

EXAMPLE 31

Synthesis of 1-[4(4-cyclopentylmethoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-21

[0170] ##STR00073##

[0171] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(cyclopentylmethoxy)phenyl)butan-1-ol II-21 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride tetrahydrofuran complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-21, with a yield of 19%. LRMS(ESI): [M+Na].sup.+601.6.

Synthesis of 1-(4-cyclopentylmethoxy)phenylbutyl-β-D-glucopyranoside IV-21

[0172] ##STR00074##

[0173] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring.

[0174] Add intermediate III-21 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-21, with a yield of 87%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.10 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.6 Hz, 2H), 4.27 (d, J=7.8 Hz, 1H), 3.99-3.86 (m, 2H), 3.83 (d, J=6.9 Hz, 2H), 3.69 (dd, J=11.8, 5.2 Hz, 1H), 3.62-3.54 (m, 1H), 3.41-3.24 (m, 3H), 3.21-3.17 (m, 1H), 2.59 (t, J=7.0 Hz, 2H), 2.40-2.30 (m, 1H), 1.93-1.78 (m, 2H), 1.76-1.57 (m, 8H), 1.47-1.35 (m, 2H). LRMS(ESI): [M+Na].sup.+433.2; HRMS(ESI): m/z Calcd for C.sub.22H.sub.34O.sub.7Na.sup.+[M+Na].sup.+: 433.2197, Found: 433.2192.

EXAMPLE 32

Synthesis of 1-[4(4-cyclohexylmethoxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-22

[0175] ##STR00075##

[0176] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(cyclohexylmethoxy)phenyl)butan- 1 -ol II-22 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride tetrahydrofuran complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-22, with a yield of 25%. LRMS(ESI): [M+Na].sup.+615.6.

Synthesis of 1-(4-cyclohexylmethoxy) phenylbutyl-β-D-glucopyranoside IV-22

[0177] ##STR00076##

[0178] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-22 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-22, with a yield of 88%. .sup.1 H NMR (400 MHz, CD.sub.3OD): δ 7.06 (d, J=8.Hz, 2H), 6.78 (d, J=8.6 Hz, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.95-3.82 (m, 2H), 3.72 (d, J=6.4 Hz, 2H), 3.66 (dd, J=11.9, 5.2 Hz, 1H), 3.59-3.50 (m, 1H), 3.37-3.20 (m, 3H), 3.19-3.12 (m, 1H), 2.56 (t, J=7.1 Hz, 2H), 1.86 (d, J=13.1 Hz, 2H), 1.81-1.57 (m, 8H), 1.38-1.16 (m, 3H), 1.09 (m, 2H). LRMS(ESI): [M+Na].sup.+447.2; HRMS(ESI): m/z Calcd for C.sub.23H.sub.36O.sub.7Na.sup.+[M+Na].sup.+: 447.2353, Found: 447.2352.

EXAMPLE 33

Synthesis of 1-[4(4-neopentyloxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-23 4-(4-(neopentyloxy)phenyl)butan-1-ol

[0179] ##STR00077##

[0180] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(neopentyloxy)phenyl)butan-1-ol II-23 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl etherate, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-23, with a yield of 15%. LRMS(ESI): [M+Na].sup.+589.2.

Synthesis of 1-(4-neopentyloxy)phenylbutyl-β-D-glucopyranoside IV-23

[0181] ##STR00078##

[0182] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-23 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-23, with a yield of 90%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.10 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.5 Hz, 2H), 4.27 (d, J=7.8 Hz, 1H), 4.01-3.82 (m, 2H), 3.71 (d, J=5.2 Hz, 1H), 3.60 (m, 3H), 3.42-3.24 (m, 4H), 3.20 (t, J=8.4 Hz, 1H), 2.59 (t, J=7.0 Hz, 2H), 1.78-1.53 (m, 4H), 1.06 (s, 9H). LRMS(ESI): [M+Na].sup.+421.1; HRMS(ESI): m/z Calcd for C.sub.21H.sub.34O.sub.7Na.sup.+[M+Na].sup.+: 421.2197, Found: 421.2194.

EXAMPLE 34

Synthesis of 1-[4(4-(3,3-dimethylbutoxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-24

[0183] ##STR00079##

[0184] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(3,3-dimethylbutoxy)phenyl)butan-1-ol II-24 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl etherate, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-24, with a yield of 18%. LRMS(ESI):[M+Na].sup.+603.2.

Synthesis of 1-(4-(3,3-dimethylbutoxy)phenyl)butyl-β-D-glucopyranoside IV-24

[0185] ##STR00080##

[0186] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-24 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-24, with a yield of 80%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.07 (d, J=8.5 Hz, 2H), 6.79 (d, J=8.6 Hz, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.99 (t, J=7.1 Hz, 2H), 3.91 (dt, J=9.3, 6.3 Hz, 1H), 3.85 (dd, J=11.9, 1.9 Hz, 1H), 3.67 (dd, J=11.9, 5.3 Hz, 1H), 3.57-3.52 (m, 1H), 3.26-3.11 (m, 4H), 2.56 (t, J=7.1 Hz, 2H), 1.75-1.53 (m, 6H), 0.99 (s, 9H). LRMS(ESI): [M+Na].sup.+435.1; HRMS(ESI): m/z Calcd for C.sub.22H.sub.36O.sub.7Na.sup.+[M+Na].sup.+: 435.2353, Found: 435.2352.

EXAMPLE 35

Synthesis of 1-[4(4-benzyloxyphenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-25

[0187] ##STR00081##

[0188] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(benzyloxy)phenyl)butan-1-ol II-25 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after concentrating organic phase to no obvious fraction, and obtain compound III-25, with a yield of 35%. LRMS(ESI): [M+Na].sup.+609.6.

Synthesis of 1-(4-benzyloxy)phenylbutyl-β-D-glucopyranoside IV-25

[0189] ##STR00082##

[0190] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-25 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-25, with a yield of 91%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.34 (m, 5H), 7.09 (d, J=8.3 Hz, 2H), 6.88 (d, J=8.4 Hz, 2H), 5.03 (s, 2H), 4.23 (d, J=7.8 Hz, 1H), 4.01-3.82 (m, 2H), 3.66 (dd, J=11.8, 5.0 Hz, 1H), 3.59-3.47 (m, 1H), 3.39-3.22 (m, 3H), 3.16 (t, J=8.3 Hz, 1H), 2.56 (t, J=6.9 Hz, 2H), 1.65 (d, J=4.1 Hz, 4H). LRMS(ESI): [M+Na].sup.+441.1; HRMS(ESI): m/z Calcd for C.sub.23H.sub.30O.sub.7Na.sup.+: 441.1884, Found: 441 .1880.

EXAMPLE 36

Synthesis of 1-[4(44(2-fluorobenzypoxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-26

[0191] ##STR00083##

[0192] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-((2-fluorobenzyl)oxy)phenyl)butan-1-ol II-26 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-26, with a yield of 37%. LRMS(ESI): [M+Na].sup.+654.23.

Synthesis of 1-[4((2-fluorobenzyl)oxy)]phenylbutyl-β-D-glucopyranoside IV-26

[0193] ##STR00084##

[0194] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-26 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-26, with a yield of 88%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.53 (td, J=7.5, 1.3 Hz, 1H), 7.42-7.34 (m, 1H), 7.21 (td, J=7.5, 1.0 Hz, 1H), 7.18-7.10 (m, 1H), 7.14 (d, J=8.6 Hz, 2H), 6.92 (d, J=8.6 Hz, 2H), 5.12 (s, 2H), 4.27 (d, J=7.8 Hz, 1H), 3.95 (dt, J=9.4, 6.3 Hz, 1H), 3.89 (dd, J=11.9, 1.8 Hz, 1H), 3.69 (dd, J=11.9, 5.2 Hz, 1H), 3.58 (dt, J=9.5, 6.3 Hz, 1H), 3.39-3.25 (m, 3H), 3.24-3.16 (m, 1H), 2.61 (t, J=7.1 Hz, 2H), 1.78-1.59 (m, 4H). LRMS(ESI): [M+Na].sup.+459.20.

EXAMPLE 37

Synthesis of 1-[4-(4-((3-fluorobenzyl)oxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-27

[0195] ##STR00085##

[0196] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-((3-fluorobenzyl)oxy)phenyl)butan-1-ol II-27 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-27, with a yield of 40%. LRMS(ESI): [M+Na].sup.+627.2.

Synthesis of 1-[4-((3-fluorobenzyl)oxy)] phenylbutyl-β-D-glucopyranoside IV-27

[0197] ##STR00086##

[0198] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-27 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-27, with a yield of 84%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.40 (dt, J=7.9, 5.9 Hz, 1H), 7.26 (d, J=7.7 Hz,1H), 7.20 (d, J=9.9 Hz, 1H), 7.13 (d, J=8.6 Hz, 2H), 7.05 (td, J=8.5, 2.3 Hz, 1H), 6.91 (d, J=8.6Hz, 2H), 5.09 (s, 2H), 4.27 (d, J=7.8 Hz, 1H), 3.95 (dt, J=9.4, 6.3 Hz, 1H), 3.89 (dd, J=11.9, 1.8 Hz, 1H), 3.69 (dd, J=11.9, 5.2 Hz, 1H), 3.62-3.54 (m, 1H), 3.41-3.24 (m, 3H), 3.23-3.15 (m, 1H), 2.60 (t, J=7.1 Hz, 2H), 1.90-1.55 (m, 4H). LRMS(ESI): [M+Na].sup.+459.2.

EXAMPLE 38

Synthesis of 1-[4-(4-((4-fluorobenzyl)oxy)phenyl) butyl]-2,3,4,6-O- tetraacetyl-β-D-glucopyranoside III-28

[0199] ##STR00087##

[0200] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-((4-fluorobenzyl)oxy)phenyl)butan-1-ol II-28 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride tetrahydrofuran complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-28 with a yield of 44%. LRMS(ESI): [M+Na].sup.+654.23.

Synthesis of 1-[4-((4-fluorobenzyl)oxy)] phenylbutyl-β-D-glucopyranoside IV-28

[0201] ##STR00088##

[0202] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-28 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) type ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-28, with a yield of 83%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7 .47 (dd, J=8.5, 5.5 Hz, 2H), 7.13 (d, J=8.6 Hz, 4H), 7.14-7.09 (m, 1H), 6.91 (d, J=8.6 Hz, 2H), 5.04 (s, 2H), 4.27 (d, J=7.8 Hz, 1H), 3.95 (dt, J=9.3, 6.2 Hz, 1H), 3.89 (dd, J=11.8, 1.7 Hz, 1H), 3.69 (dd, J=11.8, 5.2 Hz, 1H), 3.58 (dt, J=9.4, 6.2 Hz, 1H), 3.33-3.24 (m, 3H), 3.23-3.14 (m, 1H), 2.60 (t, J=7.1 Hz, 2H), 1.91-1.56 (m, 4H). LRMS(ESI): [M+Na].sup.+459.2.

EXAMPLE 39

Synthesis of 1-[4-(4-(3-(trifluoromethyebenzypoxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-29

[0203] ##STR00089##

[0204] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4((3-(trifluoromethypbenzypoxy)phenyl)butan-1-ol II-29 in turn. Cool reaction flask to 0±5° C., drop trifluoromethanesulfonic acid trimethylsilyl, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-29, with a yield of 34%. LRMS(ESI): [M+Na].sup.+677.23.

Synthesis of 1-[4-((3-(trifluoromethyl)benzypoxy)]phenylbutyl-β-D-glucopyranoside IV-29

[0205] ##STR00090##

[0206] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-29 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) type ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-29, with a yield of 81%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.74 (s, 1H), 7.69 (d, J=7.4 Hz, 1H), 7.62-7.53 (m, 2H), 7.11 (d, J=8.6 Hz, 2H), 6.91 (d, J=8.6 Hz, 2H), 5.13 (s, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.92 (dt, J=9.4, 6.3 Hz, 1H), 3.85 (dd, J=11.9, 1.7 Hz, 1H), 3.66 (dd, J=11.8, 5.2 Hz, 1H), 3.55 (dt, J=9.6, 6.2 Hz, 1H), 3.37-3.32 (m, 1H), 3.26 (t, J=5.9 Hz, 2H), 3.20-3.11 (m, 1H), 2.57 (t, J=7.1 Hz, 2H), 1.80-1.49 (m, 4H). LRMS(ESI): [M+Na].sup.+509.20.

EXAMPLE 40

Synthesis of 1- [4-(4-(4-(trifluoromethyebenzypoxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-30

[0207] ##STR00091##

[0208] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4((4-(trifluoromethypbenzypoxy)phenyl)butan-1-ol II-30 in turn. Cool reaction flask to 0±5° C., drop trifluoromethanesulfonic acid trimethylsilyl, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-30, with a yield of 40%. LRMS(ESI): [M+Na].sup.+677.2.

Synthesis of 1-[4-((4-(trifluoromethyl)benzyl)oxy)]phenylbutyl-β-D-glucopyranoside IV-30

[0209] ##STR00092##

[0210] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-30 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. After concentrating the organic phase, the final product IV-30 was obtained by column chromatography with a yield of 85%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.68 (dd, J=18.9, 8.3 Hz, 4H), 7.14 (d, J=8.6 Hz, 2H), 6.93 (d, J=8.6 Hz, 2H), 5.17 (s, 2H), 4.27 (d, J=7.8 Hz, 1H), 3.95 (dt, J=6.3, 3.3 Hz, 1H), 3.89 (dd, J=11.8, 1.7 Hz, 1H), 3.69 (dd, J=11.8, 5.2 Hz, 1H), 3.62-3.54 (m, 1H), 3.42-3.24 (m, 3H), 3.23-3.15 (m, 1H), 2.61 (t, J=7.1 Hz, 2H), 1.83-1.52 (m, 4H). LRMS(ESI): [M+Na].sup.+509.2.

EXAMPLE 41

Synthesis of 1-[4(4-(oxetan-3-ylmethoxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-31

[0211] ##STR00093##

[0212] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(oxetan-3-ylmethoxy)phenyl)butan-1-ol II-31 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl etherate, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-31, with a yield of 42%. LRMS(ESI): [M+Na].sup.+589.2.

Synthesis of 1-[4-(oxetan-3-ylmethoxy)]phenylbutyl-β-D-glucopyranoside IV-31

[0213] ##STR00094##

[0214] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-31 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) type ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-31, with a yield of 81%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 7.13 (d, J=8.5Hz, 2H), 6.88 (d, J=8.6 Hz, 2H), 4.97-4.83 (m, 2H), 4.62 (t, J=6.0 Hz, 2H), 4.27 (d, J=7.8 Hz, 1H), 4.19 (d, J=6.4 Hz, 2H), 3.95 (dt, J=6.3, 3.3 Hz, 1H), 3.89 (dd, J=11.8, 1.7Hz, 1H), 3.69 (dd, J=11.8, 5.2 Hz, 1H), 3.63- 3.54 (m, 1H), 3.52-3.41 (m, 1H), 3.41-3.24 (m, 3H), 3.23-3.15 (m, 1H), 2.61 (t, J=7.1 Hz, 2H), 1.81-1.57 (m, 4H). LRMS(ESI): [M+Na].sup.+421.1.

EXAMPLE 42

Synthesis of 1-[4(4-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-32

[0215] ##STR00095##

[0216] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)butan- 1 -ol II-32 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl etherate, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-32, with a yield of 34%. LRMS(ESI): [M+Na].sup.+617.6.

Synthesis of 1-[4-((tetrahydro-2H-pyran-4-yl)methoxy)]phenylbutyl -β-D-glucopyranoside IV-32

[0217] ##STR00096##

[0218] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-32 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-32, with a yield of 80%. .sup.1 H NMR (400 MHz, CD.sub.3OD): δ 7.11 (d, J=8.5 Hz, 2H), 6.83 (d, J=8.5 Hz, 2H), 4.27 (d, J=7.8 Hz, 1H), 4.05-3.86 (m, 4H), 3.82 (d, J=6.3 Hz, 2H), 3.69 (dd, J=11.8, 5.2 Hz, 1H), 3.58 (dt, J=9.5, 6.2 Hz, 1H), 3.49 (td, J=12.0, 1.7 Hz, 2H), 3.40-3.24 (m, 3H), 3.19 (t, J=8.4 Hz, 1H), 2.60 (t, J=7.1 Hz, 2H), 2.14-1.98 (m, 1H), 1.85-1.60 (m, 6H), 1.47 (qd, J=12.3, 4.5 Hz, 2H). LRMS(ESI): [M+Na].sup.+449.2; HRMS(ESI): m/z Calcd for C.sub.22H.sub.35O.sub.8.sup.+: 427.2326, Found: 427.2323.

EXAMPLE 43

Synthesis of 1-[4(4-(pyridin-2-yl-methoxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-33

[0219] ##STR00097##

[0220] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(pyridin-2-ylmethoxy)phenyl)butan-1-ol II-33 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-33, with a yield of 28%. LRMS(ESI): [M+Na].sup.+610.2.

Synthesis of 1-[4-(pyridin-2-yl-methoxy)]phenylbutyl-β-D-glucopyranoside IV-33

[0221] ##STR00098##

[0222] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring.

[0223] Add intermediate III-33 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-33, with a yield of 79%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 8.53 (d, J=4.4 Hz, 1H), 7.86 (td, J=7.8, 1.6 Hz, 1H), 7.59 (d, J=7.9 Hz, 1H), 7.36 (dd, J=7.0, 5.4 Hz, 1H), 7.10 (d, J=8.6 Hz, 2H), 6.90 (d, J=8.6 Hz, 2H), 5.13 (s, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.95-3.88 (m, 1H), 3.85 (dd, J=11.9, 1.7 Hz, 1H), 3.66 (dd, J=11.9, 5.2 Hz, 1H), 3.59-3.51 (m, 1H), 3.35-3.12 (m, 4H), 2.57 (t, J=7.1 Hz, 2H), 1.81-1.52 (m, 4H). LRMS(ESI): [M+Na].sup.+442.0; HRMS(ESI): m/z Calcd for C.sub.22H.sub.29O.sub.7NNa.sup.+[M+Na].sup.+: 442.1836, Found: 442.1834.

EXAMPLE 44

Synthesis of 1-[4(4-(pyridin-3-yl-methoxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-34

[0224] ##STR00099##

[0225] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(pyridin-3-ylmethoxy)phenyl)butan-1-ol II-34 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-34, with a yield of 31%. LRMS(ESI): [M+Na].sup.+610.6.

Synthesis of 1-[4-(pyridin-3-yl-methoxy)]phenylbutyl -β-D-glucopyranoside IV-34

[0226] ##STR00100##

[0227] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-34 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-34, with a yield of 85%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 8.65 (d, J=1.2 Hz, 1H), 8.52 (dd, J=4.9, 1.2 Hz, 1H), 7.96 (d, J=7.9 Hz, 1H), 7.48 (dd, J=7.8, 5.0 Hz, 1H), 7.14 (d, J=8.5 Hz, 2H), 6.94 (d, J=8.6 Hz, 2H), 5.14 (s, 2H), 4.27 (d, J=7.8 Hz, 1H), 3.99-3.85 (m, 2H), 3.69 (dd, J=11.9, 5.2 Hz, 1H), 3.58 (dt, J=9.4, 6.2 Hz, 1H), 3.43-3.24 (m, 3H), 3.23-3.16 (m, 1H), 2.60 (t, J=7.1 Hz, 2H), 1.76-1.60 (m, 4H). LRMS(ESI): [M+Na].sup.+442.1; HRMS(ESI): m/z Calcd for C.sub.22H.sub.29O.sub.7NNa.sup.+[M+Na].sup.+: 442.1836, Found: 442.1834.

EXAMPLE 45

Synthesis of 1-[4(4-(pyridin-4-yl-methoxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-35

[0228] ##STR00101##

[0229] Operation steps: Replace reaction flask with nitrogen for 3 times, add toluene as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(pyridin-4-ylmethoxy)phenyl)butan-1-ol II-35 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride ether complex, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-35, with a yield of 36%. LRMS(ESI): [M+Na].sup.+610.6.

Synthesis of 1-[4-(pyridin-4-yl-methoxyl)]phenylbutyl-β-D-glucopyranoside IV-35

[0230] ##STR00102##

[0231] Operation steps: Replace reaction flask with nitrogen for 3 times, add methanol as solvent, and start stirring. Add intermediate III-35 into reaction flask, control temperature at 25±5° C., add sodium methoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after methanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain final product IV-35, with a yield of 90%. .sup.1H NMR (400 MHz, CD.sub.3OD): δ 8.66-8.44 (m, 2H), 7.54 (d, J=5.9 Hz, 2H), 7.15 (d, J=8.6 Hz, 2H), 6.93 (d, J=8.6 Hz, 2H), 5.18 (s, 2H), 4.26 (d, J=7.8 Hz, 1H), 3.95 (dt, J=9.5, 6.3 Hz, 1H), 3.89 (dd, J=11.9, 1.9 Hz, 1H), 3.69 (dd, J=11.8, 5.2 Hz, 1H), 3.62-3.54 (m, 1H), 3.41-3.24 (m, 3H), 3.23-3.16 (m, 1H), 2.61 (t, J=7.1 Hz, 2H), 1.77-1.58 (m, 4H). LRMS(ESI): [M+1-1]±420.2; HRMS(ESI): m/z Calcd for C.sub.22H.sub.30O.sub.7N.sup.+[M+H].sup.+: 420.2017, Found: 420.2014.

EXAMPLE 46

Synthesis of 1-[4(4-(hexadecyloxy)phenyl)butyl]-2,3,4,6-O- tetraacetyl -β-D-glucopyranoside III-36

[0232] ##STR00103##

[0233] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-(hexadecyloxy)phenyl)butan-1-ol II-36 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl etherate, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-36, with a yield of 37%. LRMS(ESI): [M+Na].sup.+743.4.

Synthesis of 1[4-(hexadecyloxy)]phenylbutyl-β-D-glucopyranoside IV-36

[0234] ##STR00104##

[0235] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-36 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain compound IV-36, with a yield of 78%. i H NMR (400 MHz, CD.sub.3OD) δ 7.07 (d, J=8.6 Hz, 2H), 6.79 (d, J=8.6 Hz, 2H), 4.23 (d, J=7.8 Hz, 1H), 3.92 (dd, J=7.9, 5.1 Hz, 2H), 3.85 (dd, J=11.9, 1.9 Hz, 1H), 3.66 (dd, J=11.9, 5.2 Hz, 1H), 3.55 (m, 1H), 3.34-3.21 (m, 4H), 2.56 (t, J=7.1 Hz, 2H), 1.70 (m, 6H), 1.45 (m, 2H), 1.41-1.20 (m, 24H), 0.99 (s, 1H), 0.89 (t, J=6.8 Hz, 3H). LRMS(ESI): [M+Na].sup.+575.3; HRMS(ESI): m/z Calcd for C.sub.32H.sub.56O.sub.7Na.sup.+[M+Na].sup.+: 575.3918, Found: 575.3917.

EXAMPLE 47

Synthesis of 1-[4-(4((2,5,8,11-tetraoxatridecan-13-yeoxy)phenyl)butyl]-2,3,4,6-O-tetraacetyl-β-D-glucopyranoside III-37

[0236] ##STR00105##

[0237] Operation steps: Replace reaction flask with nitrogen for 3 times, add dichloromethane as solvent, and start stirring. Then, add β-D-glucose pentaacetate I and 4-(4-((2,5,8,11-tetraoxatridecan-13-yl)oxy)phenyl)butan-1-ol II-37 in turn. Cool reaction flask to 0±5° C., drop boron trifluoride dibutyl etherate, and continue to stir for 12 h after that. After reaction, drop water to system to quench, separate liquid, wash organic phase with Na.sub.2CO.sub.3 water solution, separate liquid, and wash organic phase with water once again. Collect organic phase after liquid separation. Conduct column chromatography isolation after organic phase concentration, and obtain compound III-37, with a yield of 30%. LRMS(ESI): [M+Na].sup.+709.3.

Synthesis of 1-[4-((2,5,8,11-tetraoxatridecan-13-yl)oxy)]phenylbutyl-β-D-glucopyranoside IV-37

[0238] ##STR00106##

[0239] Operation steps: Replace reaction flask with nitrogen for 3 times, add ethanol as solvent, and start stirring. Add intermediate III-37 into reaction flask, control temperature at 25±5° C., add sodium ethoxide into reaction flask, and stir to react for 2 h. After reaction, conduct diatomite filtration, and collect filtrate after ethanol leaching. Add (H.sup.+) ion exchange resin and stir for 10 h. Filter to remove (H.sup.+) ion exchange resin. Conduct column chromatography isolation after organic phase concentration, and obtain compound IV-37, with a yield of 81%. .sup.1H NMR (400 MHz, CD.sub.3OD) δ 7.08 (d, J=8.5 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 4.23 (d, J=7.8 Hz, 1H), 4.15-4.02 (m, 2H), 3.91 (m, 1H), 3.85 (dd, J=11.8, 1.7 Hz, 1H), 3.83-3.78 (m, 2H), 3.71-3.47 (m, 14H), 3.36-3.17 (m, 7H), 2.56 (t, J=7.0 Hz, 2H), 1.66 (m, 4H). LRMS(ESI): [M+Na].sup.+541.2; HRMS(ESI): m/z Calcd for C.sub.25H.sub.42O.sub.11Na.sup.+[M+Na].sup.+: 541.2619, found: 541.2618.

[0240] The above description is a general description of the invention. According to the situation or actual needs, the change of form and equivalent substitution can be conducted. Although specific terms are used herein, these terms are used for description, not for restriction. Technicians in this filed can make changes or modifications to the present invention, and these equivalent forms also fall within the scope defined by the attached claims of this application.