Selective synthesis of anomeric α-glycosyl acetamides via intramolecular Staudinger ligation of the α-azides

alpha-Glycosyl azides can be transformed into the corresponding alpha-glycosyl acetamides with complete retention of configuration via reduction-acylation (Staudinger ligation) reactions using specifically functionalized phosphines. The of alpha-acetamides of per-O-benzylated-fucose, per-O-benzylated-glucose and per-O-benzylated-galactose were selectively synthesized by this process. (C) 2004 Elsevier Ltd. All rights reserved.