title: Use of N,O-dimethylhydroxylamine as an anomeric protecting group in carbohydrate synthesis.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, Canada M5S 3H6.
authors.forename: Somnath
authors.initials: S
authors.lastname: Dasgupta
authors.forename: Mark
authors.initials: M
authors.lastname: Nitz
mesh_terms: D004123:Dimethylamines / Q000737:chemistry*; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004123:Dimethylamines; D009844:Oligosaccharides; C558817:N,O-dimethylhydroxylamine