Oxazolidinone protection of N-acetylglucosamine confers high reactivity on the 4-hydroxy group in glycosylation

Abstract

[reaction: see text] The preparation of a convenient oxazolidinone protected N-acetyl glucosamine 4-OH derivative is reported. This substance exhibits enhanced reactivity as a glycosyl acceptor in a variety of coupling methods, the products of which are converted to the target N-acetylglucosaminyl saccharides under very mild conditions.