Order of Reactivity of OH/NH Groups of Glucosamine Hydrochloride and N-Acetyl Glucosamine Toward Benzylation Using NaH/BnBr in DMF

摘要

The order of reactivity of OH and NH groups of glucosamine hydrochloride (GlcNH(2)(.)HCl) and N-acetyl glucosamine (GlcNAc) toward benzylation with NaH/BnBr in DMF was investigated. For GlcNH(2)(.)HCl, benzyl groups were introduced in the order of N-Bn > N-Bn-2 > 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn; for GlcNAc, benzyl groups were introduced in the order of 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn > N-Bn. A range of partially benzylated 2-N,N-dibenzyl glucopyranosides and GlcNAc derivatives were obtained in a single step.