Synthesis of ester-and amide-linked pseudo-azadisaccharides via coupling of D-glucose with 6-amino-6-deoxy-2,5-imino-D-glucitol

Abstract

Hydrolytically-resistant pseudodisaccharides incorporating an azafuranose have been prepared by coupling 6-amino-2,5-imino-D-glucitol derivatives with D-glucose, either through an ester or an amide bond. Synthesis of the azasugar templates was achieved by nucleophilic opening of a C2 symmetric bis-aziridine deriving from D-mannitol.