Studies on Carbohydrates. IX Highly Stereoselective Approach to 1-O-Acyl-D-glucopyranose by Using Glucosyl Trimethylsilyl Ether as an Intermediate

Abstract

Model reaction of α-D-glucopyranosyl trimethylsilyl ether 1 with a series of acids demonstrated that stereocontrolled glucosyl transfer with the retention of configuration at the anomeric center is best carried out in dichloromethane at room temperature with boron trifluoride-ether as a Lewis acid catalyst. Under these conditions, I-O-acyl-α-D-glucopyranoses were obtained in good yield.