METHODS FOR THE STEREOSELECTIVE PREPARATION AND SEPARATION OF TRI-O-ACETYL-5-DEOXY-BETA;-D-RIBOFURANOSE

摘要

A method for preparing tri-O-acetyl-5-deoxy-beta-D-ribofuranose is provided to separate and obtain the tri-O-acetyl-5-deoxy-beta-D-ribofuranose easily and purely from a beta-/alpha-anomer mixture of tri-O-acetyl-5-deoxy-D-ribofuranose by using an alkyl amine-based or cyclic amine-based base instead of pyridine during acetylation. A method for preparing tri-O-acetyl-5-deoxy-beta-D-ribofuranose represented by a formula(1) comprises the steps of: (a) reacting a compound represented by a formula(3) with an acetic acid anhydride in an organic solvent in the presence of an alkyl amine-based or cyclic amine-based base to prepare a compound represented by a formula(2); and (b) crystallizing the compound of the formula(2) using a solvent and an anti-solvent to isolate a beta-anomer therefrom, wherein the alkyl amine-based or cyclic amine-based base is selected from the group consisting of triethyl amine, n-tributyl amine, dicyclohexylamine, tetramethylethylenediamine, diisopropylethylamine, N-methyl morpholine and a mixture thereof. Further, the solvent is isopropanol and the anti-solvent is n-hexane or water.