Access to Homoglyconojirimycins via Ring Isomerisation of Penta­hydroxylated Azepanes

Abstract

N-Benzyl pentahydroxyazepanes undergo ring isomerization during mesylation of the hydroxyl group β to the nitrogen via a neighboring nitrogen participation involving a transient aziridinium species which is trapped by chlorine. The resulting chloro­methyl tetrahydroxypiperidines have been converted into the corresponding homoglyconojirimycins.

Key words

azasugars - aziridinium - glycosidases - piperidines - ring contractions

References and Notes

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