THE PREPARATION METHOD OF 2-DEOXY-L-RIBOSE

摘要

A preparation method of 2-deoxy-L-ribose useful as a major intermediate of L-nucleoside as an antiviral agent is provided to improve economical efficiency and preparation yield, so that 2-deoxy-L-ribose is produced in an industrial scale inexpensively. A preparation method of 2-deoxy-L-ribose represented by a formula(I) comprises the steps of: acylating or halogenizing L-arabinose represented by the formula(1) to prepare 1-halo-2,3,4-triacyl compounds represented by a formula(5); reacting the 1-halo-2,3,4-triacyl compounds represented by the formula(5) with zinc in the presence of ethyl acetate and organic base to prepare glycal represented by a formula(6); treating the glycal represented by the formula(6) with alcohol under acid condition to prepare 1-alkoxy-2-deoxy-3,4-diacyl-L-ribopyranose represented by a formula(7); treating the 1-alkoxy-2-deoxy-3,4-diacyl-L-ribopyranose represented by the formula(7) with base to prepare 1-alkoxy-2-deoxy-L-ribopyranose represented by a formula(8); and hydrolyzing the 1-alkoxy-2-deoxy-L-ribopyranose represented by the formula(8) under acid catalyst, wherein R1 is lower alkyl, R2', R3' and R4' are each independently arylacyl group or halogen-substituted arylacyl group, and Hal is halogen. Further, the acylating is performed by reacting the L-arabinose with acylchloride in the pyridine solution.