title: A new method for the stereoselective synthesis of alpha- and beta-glycosylamines using the Burgess reagent.
abstract: Although glycosylamines constitute an important group of carbohydrates from the standpoint of biology and medicine, methods for their synthesis typically lack substrate generality and/or result in variable stereoselectivity, especially in complex contexts. In this communication, we report an operationally simple method for the synthesis of both alpha- and beta-glycosylamines using the Burgess reagent that overcomes many of these limitations in a bare minimum of synthetic steps.
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. kcn@scripps.edu
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: Scott A
authors.initials: SA
authors.lastname: Snyder
authors.forename: Annie Z
authors.initials: AZ
authors.lastname: Nalbandian
authors.forename: Deborah A
authors.initials: DA
authors.lastname: Longbottom
mesh_terms: D000606:Amino Sugars / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000737:chemistry; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D000606:Amino Sugars; D002241:Carbohydrates; D007202:Indicators and Reagents