Use of N, O-Dimethylhydroxylamine As an Anomeric Protecting Group in Carbohydrate Synthesis

摘要

The N, O-dimethyloxyamine-N-glycosides are introduced as anomerically protected building blocks for carbohydrate synthesis. These N-glycosides are stable to a variety of protecting group manipulations including acylation, alkylation, silylation, and acetal formation. The alkoxyamine-N-glycosides can be cleaved selectively with N-chlorosuccinimide to give the desired hemiacetals in excellent yield. Furthermore, these N-glycosides are stable to the activation conditions required for glycosylation using thioglycoside and trichloroacetimidate glycosyl donors suggesting N, O-dialkoxyamine-N-glycosides will be useful for complex oligosaccharide synthesis.