N-Thiocarbonyl azasugars: a new family of carbohydrate mimics with controlled anomeric configuration

Abstract

Bicyclic azasugar glycomimetics structurally related to the polyhydroxy-indolizine and -piperidine series incorporating a stereoelectronically controlled pseudoanomeric axial hydroxy group have been prepared by tautomeric rearrangement of cyclic thiocarbamate precursors; preliminary enzyme inhibition tests show an increased selectivity towards yeast α-glucosidase for the α-D-glucopyranose analogue as compared with castanospermine or nojirimicin.

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