Access to Homoglyconojirimycins via Ring Isomerisation of Penta­hydroxylated Azepanes

Tao Liu; Yongmin Zhang; Yves Blériot

doi:10.1055/s-2007-973884

LETTER

Access to Homoglyconojirimycins via Ring Isomerisation of Pentahydroxylated Azepanes

Tao Liu^a,b, Yongmin Zhang^a,b, Yves Blériot*^a
^a Ecole Normale Supérieure, Département de Chimie, Institut de Chimie Moléculaire (FR 2769), UMR 8642, CNRS-ENS-UPMC Paris 6, 24 Rue Lhomond, 75231 Paris Cedex 05, France
Fax: +33(1)44323397; e-Mail: yves.bleriot@ens.fr;
^b ZJU-ENS Joint Laboratory of Medicinal Chemistry, School of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. of China

Abstract

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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

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References

References and Notes

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Access to Homoglyconojirimycins via Ring Isomerisation of Penta­hydroxylated Azepanes

Access to Homoglyconojirimycins via Ring Isomerisation of Pentahydroxylated Azepanes