Synthesis of 2,4-diacetamido-2,4,6-trideoxy-D-glucose and its identification with the diacetamido-sugar of Bacillus licheniformis

Abstract

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (1a) obtained from 2-acetamido-2-deoxy-D-glucose was converted into benzyl 2-acetamido-3-O-benzyl-1-2,6-dideoxy-α-D-glucopyranoside (2e); double inversion of configuration at C-4 in (2e) with introduction of an amino-group via the corresponding azide followed by N-acetylation and removal of the benzyl groups gave 2,4-diacetamido-2,4,6-trideoxy-D-glucose (4), found to be identical with the diacetamido-sugar of B. licheniformis.