A New Approach for Preparing Methyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-alpha-D-glucopyranoside

Abstract

Azide sugars are key intermediates in the synthesis of aminglycosides, which themselves are useful for the synthesis of glycopeptides. A new method has been achieved by using DPPA and DBU in dry DMF with high temperature for replacement of the azide group from alcohol (glucoside) on the position 6. The results of this method are very important for preparing 6-azido sugar without needing to prepare and separate glucosyl halide completely. The proposed method was successfully applied with direct, simple, and time saving. In addition, excellent yield of 95% was obtained from azide, which could be used to obtain pharmaceutical active compounds.

Keywords: Methyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-?-D-glucopyranoside, DPPA, DBU, azides.