Preparation of diamino pseudodisaccharide derivatives from 1,6-anhydro-β- d-hexopyranoses via aziridine-ring cleavage

Abstract

Twelve positional isomers of diamino pseudodisaccharide derivatives with gluco–gluco configuration have been prepared using aziridine-ring cleavage of epimino derivatives of 1,6-anhydro-β- d-hexopyranoses of the d- allo, d- manno, and d- galacto configuration by 2-, 3-, and 4-amino derivatives of 1,6-anhydro-β- d-glucopyranose. The N-substitution of the aziridine ring by a 2-nitrobenzenesulfonyl group and ionic-liquid solvent ( N-methylpyridinium tosylate) was used to obtain cleavage products in high yield (64–93%). The cleavage reactions proceeded according to the Fürst–Plattner rule and only trans-diaxial stereoisomers were formed.