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

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.

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