Tandem Staudinger-azaWittig mediated ring expansion: rapid access to new isofagomine-tetrahydroxyazepane hybrids

Hongqing Li; Yongmin Zhang; Pierre Vogel; Pierre Sinaÿ; Yves Blériot

doi:10.1039/b610377d

Tandem Staudinger-azaWittig mediated ring expansion: rapid access to new isofagomine-tetrahydroxyazepane hybrids

Chem Commun (Camb). 2007 Jan 14:(2):183-5. doi: 10.1039/b610377d. Epub 2006 Oct 24.

Authors

Hongqing Li¹, Yongmin Zhang, Pierre Vogel, Pierre Sinaÿ, Yves Blériot

Affiliation

¹ Ecole Normale Supérieure, Département de Chimie, UMR 8642, Université Pierre et Marie Curie-Paris 6, 75005 Paris, France.

PMID: 17180240
DOI: 10.1039/b610377d

Abstract

New seven-membered iminosugars with potent and selective inhibition towards glycosidases have been prepared as 1-N-iminosugar homologues via a tandem Staudinger-azaWittig mediated ring expansion.

MeSH terms

Azepines / chemistry*
Cellulases / antagonists & inhibitors
Cellulases / chemistry
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / chemistry
Glucan 1,4-alpha-Glucosidase / antagonists & inhibitors
Glucan 1,4-alpha-Glucosidase / chemistry
Glycoside Hydrolases / antagonists & inhibitors
Glycoside Hydrolases / chemistry
Imino Pyranoses / chemistry
Imino Sugars / chemical synthesis*
Imino Sugars / chemistry
Molecular Structure
Piperidines / chemistry*
alpha-Mannosidase / antagonists & inhibitors
alpha-Mannosidase / chemistry

Substances

3,4,5,6-tetrahydroxyazepane
Azepines
Enzyme Inhibitors
Imino Pyranoses
Imino Sugars
Piperidines
isofagomine
Cellulases
Glycoside Hydrolases
alpha-Mannosidase
Glucan 1,4-alpha-Glucosidase