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

Peter Maier; Søren Møller Andersen; Inge Lundt

doi:10.1055/s-2006-926343

PAPER

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;

Abstract

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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.

Key words

chiral pool - azasugars - glycosidase inhibitors - ring opening

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References

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