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  • Title: Preparation of diamino pseudodisaccharide derivatives from 1,6-anhydro-beta-D-hexopyranoses via aziridine-ring cleavage.
    Author: Kroutil J, Budesínský M.
    Journal: Carbohydr Res; 2007 Feb 05; 342(2):147-53. PubMed ID: 17204257.
    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-beta-D-hexopyranoses of the D-allo, D-manno, and D-galacto configuration by 2-, 3-, and 4-amino derivatives of 1,6-anhydro-beta-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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