Provided herein include sulfated glycosaminoglycans including sulfated disaccharides, tetrasaccharides, and oligosaccharides and methods of synthesizing heparan sulfate disaccharide, tetrasaccharide, oligosaccharide library in solution-phase. Provided herein also includes a method of treating neurological diseases or disorders with sulfated glycosaminoglycans such as 4-O-sulfated chondroitin sulfate polysaccharides.

A fucosylated chondroitin sulfate oligosaccharide having the structure as shown in J, and further disclosed is a method for preparing the fucosylated chondroitin sulfate oligosaccharide: using a chondroitin sulfate A salt as a raw material, sequentially performing enzymolysis, a group protection operation, and glycosylation to synthesize the oligosaccharide compound; the certainty of the described structure allows said oligosaccharide to be applied to the medical field. ##STR00001##

A fucosylated chondroitin sulfate oligosaccharide having the structure as shown in J, and further disclosed is a method for preparing the fucosylated chondroitin sulfate oligosaccharide: using a chondroitin sulfate A salt as a raw material, sequentially performing enzymolysis, a group protection operation, and glycosylation to synthesize the oligosaccharide compound; the certainty of the described structure allows said oligosaccharide to be applied to the medical field. ##STR00001##

This application relates to efficient methods for the synthesis of ascarylose and its derivatives. A method for the production of ascarylose includes: providing, as a feedstock, a 1-O-substituted rhamnose; forming a mono-sulfonate ester at the 3-OH group of the 1-O-substituted rhamnose; and treating the mono-sulfonate ester with a hydride source to form a 1-O-substituted ascarylose. Forming the mono-sulfonate ester can advantageously be conducted on a 1-O-substituted rhamnose without hydroxyl protecting groups at either the 2-OH or 4-OH-positions.

A purpose of the present invention is to provide a method for producing a glycoside compound having a high purity. The present invention provides a method for producing a glycoside compound represented by formula (3) (wherein B.sup.a, i-Pr and n are the same as those defined below), which comprises reacting a glycoside compound of formula (1) (wherein B.sup.a represents an adenine group which may be optionally substituted with an acyl group, and i-Pr represents an isopropyl group) with an ether compound of formula (2) (wherein R.sup.1 represents a C1-C6 alkyl group or a phenyl group, and n is 0 or 1) in one or more solvents selected from tetrahydropyran and 4-methyltetrahydropyran in the presence of one or more halogenated agents selected from halogen, N-halogenated succinimide, and N-halogenated hydantoin. ##STR00001##

A purpose of the present invention is to provide a method for producing a glycoside compound having a high purity. The present invention provides a method for producing a glycoside compound represented by formula (3) (wherein B.sup.a, i-Pr and n are the same as those defined below), which comprises reacting a glycoside compound of formula (1) (wherein B.sup.a represents an adenine group which may be optionally substituted with an acyl group, and i-Pr represents an isopropyl group) with an ether compound of formula (2) (wherein R.sup.1 represents a C1-C6 alkyl group or a phenyl group, and n is 0 or 1) in one or more solvents selected from tetrahydropyran and 4-methyltetrahydropyran in the presence of one or more halogenated agents selected from halogen, N-halogenated succinimide, and N-halogenated hydantoin. ##STR00001##