Issue 9, 2006
From the journal:

Organic & Biomolecular Chemistry

Nucleophilic opening of epoxyazepanes: expanding the family of polyhydroxyazepane-based glycosidase inhibitors†

Hongqing Li,ac   Catherine Schütz,b   Sylvain Favre,b   Yongmin Zhang,ac   Pierre Vogel,b   Pierre Sinaÿac  and  Yves Blériot*ac  

* Corresponding authors

a Ecole Normale Supérieure, Département de Chimie, UMR 8642 associée au CNRS, 24 rue Lhomond, Paris Cedex 05, France
E-mail: yves.bleriot@ens.fr
Fax: +33 1 44 32 33 97
Tel: +33 1 44 32 33 35

b Laboratoire de glycochimie et de synthèse asymétrique, Swiss Federal Institute of Technology (EPFL) BCH, Lausanne-Dorigny, Switzerland

c Institut de Chimie Moléculaire (FR 2769), Université Pierre et Marie Curie-Paris 6, Paris, France

Abstract

A range of new tetra- and pentahydroxylated seven-membered iminoalditols has been efficiently synthesized from epoxyazepane precursors via nucleophilic opening with hydride or oxygenated species and subsequent hydrogenolysis. One tetrahydroxylated azepane, a ring homologue of deoxymannojirimycin, displays a selective and fairly good inhibition of α-L-fucosidase.

Graphical abstract: Nucleophilic opening of epoxyazepanes: expanding the family of polyhydroxyazepane-based glycosidase inhibitors

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Article information

DOI
https://doi.org/10.1039/B518117H
Article type
Paper
Submitted
04 Jan 2006
Accepted
01 Mar 2006
First published
28 Mar 2006

Org. Biomol. Chem., 2006,4, 1653-1662

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Nucleophilic opening of epoxyazepanes: expanding the family of polyhydroxyazepane-based glycosidase inhibitors

H. Li, C. Schütz, S. Favre, Y. Zhang, P. Vogel, P. Sinaÿ and Y. Blériot, Org. Biomol. Chem., 2006, 4, 1653 DOI: 10.1039/B518117H

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