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Synlett 2007(6): 0905-0908  
DOI: 10.1055/s-2007-973884
LETTER
© Georg Thieme Verlag Stuttgart · New York

Access to Homoglyconojirimycins via Ring Isomerisation of Penta­hydroxylated Azepanes

Tao Liua,b, Yongmin Zhanga,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
Further Information

Publication History

Received 12 January 2007
Publication Date:
26 March 2007 (online)

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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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