PRODUCTION OF 1,6-ANHYDRO-2,3,4-TRIDEOXY-BETA-D-GLYCERO-HEXO-3-ENOPYRANOSE

摘要

PURPOSE: To obtain the subject compound useful as a raw material for synthesizing saccharides or a raw material for polymers by using a D-glucal of an inexpensive raw material and a reagent. ;CONSTITUTION: A 3,4,6-tri-0-acyl-D-glucal of formula I (R¹ is acetyl or benzoyl) is reacted with a phenol derivative to give an enopyranoside of formula II (Ph is phenyl). Then 0-acyl group is hydrolyzed and the resulting substance is subjected to ring formation at the 1- and the 6-positions to give a 1,6- anhydroenopyranose derivative of formula III. The double bond of the compound of formula III is reduced by adding hydrogen to give a 1,6-anhydropyranose derivative of formula IV and then hydroxyl group at the 4-position is protected to give a compound of formula V (R² is p-toluenesulfonyl, mesyl or acetyl). Hydrogen at the 3-position and the substituent group at the 4-position are eliminated to give the objective substance of formula VI.;COPYRIGHT: (C)1993,JPO&Japio