Synthesis 2006(5): 827-830  
DOI: 10.1055/s-2006-926343
PAPER
© Georg Thieme Verlag Stuttgart · New York

1,5-Anhydro-d-fructose as Chiral Building Block: A Novel Approach to 1-Deoxymannojirimycin

Peter Maier, Søren Møller Andersen, Inge Lundt*
Department of Chemistry, Technical University of Denmark, Building 201, 2800 Lyngby, Denmark
Fax: +4545933968; e-Mail: il@kemi.dtu.dk;
Further Information

Publication History

Received 2 August 2005
Publication Date:
08 February 2006 (online)

Abstract

A novel six-step synthesis of 1-deoxymannojirimycin from 1,5-anhydro-d-fructose in 35% overall yield is reported. The key steps are nucleophilic piperidine ring formation and subsequent Lewis acid induced pyran ether cleavage.