A new method for the stereoselective synthesis of alpha- and beta-glycosylamines using the Burgess reagent.
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.
Nicolaou
K C
KC
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
Snyder
Scott A
SA
Nalbandian
Annie Z
AZ
Longbottom
Deborah A
DA
D000606:Amino Sugars / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000737:chemistry; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D000606:Amino Sugars; D002241:Carbohydrates; D007202:Indicators and Reagents