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Synthesis 2006(5): 827-830
DOI: 10.1055/s-2006-926343
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
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.
Key words
chiral pool - azasugars - glycosidase inhibitors - ring opening