Glycosylation Using 2-Azido-3,4,6-tri-<i>O</i>-benzyl-2-deoxy-<scp>d</scp>-glucose, -galactose, and -mannose with the Aid of <i>p</i>-Nitrobenzenesulfonyl Chloride–Silver Trifluoromethanesulfonate–Triethylamine System

Abstract

Abstract This report describes a simple synthesis of 2-azido-3,4,6-tri-O-benzyl-2-deoxy-d-glucopyranose. Glycosylation using this as well as 2-azido-3,4,6-tri-O-benzyl-2-deoxy-d-galactopyranose and -mannopyranose was achieved with the aid of a reagent system consisting of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, and its modifications. O-(2-Acetamido-2-deoxy-β-d-glucopyranosyl)-(1→4)-O-α-d-mannopyranosyl-(1→4)-α-d-mannopyranose, the repeating unit of the main chain of the O-specific cell wall polysaccharide of E. coli 058 was synthesized.