The invention relates to the field of pharmaceutical synthesis, in particular to the preparation method of hexahydrofuro-furanol derivative, intermediates thereof and preparation methods thereof. The preparation methods comprises the steps of halogenation reaction, acylation reaction, enzymatic reduction reaction, reaction with amine compounds, reduction ring closure reaction (A1, A2, B, Cp1, C.sub.L, Cf)

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wherein, R.sub.1, R.sub.2, R.sub.3 are hydrogen or hydroxy protecting groups; R.sub.4 and R.sub.5 are the same or different and are phenyl, alkyl or substituted phenyl. In the preparation process of hexahydrofuro-furanol derivatives, the chirality is constructed by enzymatic method, and the product can be prepared with very high optical purity by adopting such technical means. The preparation method can be used to prepare the key intermediate, (3R, 3aS, 6aR)-hexahydrofuro[2,3-b]-3-ol, of Darunavir, in commercial production, which is a very economical route suitable for industrial production.

The invention is related to a composition excellent in stability during storage and excellent stability during utilization, and related to a method of producing the composition. The composition comprises a compound (A) represented by general formula (1) and a compound (B). The compound (B) is an oligomer in which two or more molecules of the compound (A) are bonded to each other by ethylenically unsaturated groups of each compound (A). The composition contains 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),

(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m  (1)

wherein in general formula (1), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contain an ether group; and n and in each represent an integer of one or two.

The invention is related to a composition excellent in stability during storage and excellent stability during utilization, and related to a method of producing the composition. The composition comprises a compound (A) represented by general formula (1) and a compound (B). The compound (B) is an oligomer in which two or more molecules of the compound (A) are bonded to each other by ethylenically unsaturated groups of each compound (A). The composition contains 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),

(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m  (1)

wherein in general formula (1), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contain an ether group; and n and in each represent an integer of one or two.

The invention relates to a composition excellent in stability during storage and stability during utilization, and relates to a method of producing the composition. The composition includes a compound (A) represented by general formula (1) and a compound (B) represented by general formula (2), and includes 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),

(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m  (1)

(R.sub.1—COO).sub.n—R.sub.2—(R.sub.3—R.sub.1).sub.m  (2)

wherein in general formulae (1) and (2), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contains an ether group; R.sub.1 and R.sub.2 in the general formula (1) are the same as R.sub.1 and R.sub.2 in the general formula (2); in general formula (2), R.sub.3 is —NHC(═O)—; and n and m each represent an integer of one or two.

The invention relates to a composition excellent in stability during storage and stability during utilization, and relates to a method of producing the composition. The composition includes a compound (A) represented by general formula (1) and a compound (B) represented by general formula (2), and includes 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),

(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m  (1)

(R.sub.1—COO).sub.n—R.sub.2—(R.sub.3—R.sub.1).sub.m  (2)

wherein in general formulae (1) and (2), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contains an ether group; R.sub.1 and R.sub.2 in the general formula (1) are the same as R.sub.1 and R.sub.2 in the general formula (2); in general formula (2), R.sub.3 is —NHC(═O)—; and n and m each represent an integer of one or two.

This invention provides illudin derivatives, intermediates, preparation methods, pharmaceutical compositions and uses thereof. Specific examples include novel synthetic routes to prepare illudin derivatives and an illudin derivative having a positive optical rotation, which has therapeutic value.

Provided is a method for producing a perfluoroalkylated compound at low cost, safely and with high efficiency. A method for producing a perfluoroalkylated compound, comprising reacting a bis(perfluoroalkanoyl) peroxide with a compound having a carbon-carbon unsaturated bond and/or an aromatic ring having a hydrogen atom bonded thereto in the presence of a copper catalyst.

Provided is a method for producing a perfluoroalkylated compound at low cost, safely and with high efficiency. A method for producing a perfluoroalkylated compound, comprising reacting a bis(perfluoroalkanoyl) peroxide with a compound having a carbon-carbon unsaturated bond and/or an aromatic ring having a hydrogen atom bonded thereto in the presence of a copper catalyst.

A novel method for synthesizing deuterated amides and deuterated sulfonamides includes the following steps: (1) adding a compound M, DMAP, R.sup.3—X to a solvent to obtain a compound N after a reaction is complete; and (2) adding the compound N, R.sup.4—NH—R.sup.5, or a salt and base thereof to a solvent, and purifying after a reaction is complete to obtain a compound I.

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A novel method for synthesizing deuterated amides and deuterated sulfonamides includes the following steps: (1) adding a compound M, DMAP, R.sup.3—X to a solvent to obtain a compound N after a reaction is complete; and (2) adding the compound N, R.sup.4—NH—R.sup.5, or a salt and base thereof to a solvent, and purifying after a reaction is complete to obtain a compound I.

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