Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: application to the synthesis of thiooligosaccharides

Abstract

The cyclic sulfamidate of the allosamine derivative 11 is efficiently prepared by reaction with 1,1′-sulfuryl diimidazole; the regioselective opening of this compound by sulfur nucleophiles furnishes 3-thioglucosamine derivatives, useful intermediates in synthesis of thiooligosaccharides.