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Journal of Carbohydrate Chemistry Volume 30, 2011 - Issue 7-9: European Young Investigator Workshop. “Carbohydrate Chemistry: From Synthesis to Applications,” Lyon, France, 2011
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Original Articles

Synthesis of 1-Deoxynojirimycin Derivatives from L-Sorbose via Wittig Reactions

Colin O’ Brien Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland
&
Paul V. Murphy School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland
Pages 626-640 | Received 25 Jul 2011, Accepted 29 Aug 2011, Published online: 14 Dec 2011
 
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Abstract

A strategy for the synthesis of 1-deoxynojirimycin (DNJ) derivatives from L-sorbose is described. The sequence involved eight steps and afforded DNJ derivatives in 13% to 44% overall yield.

ACKNOWLEDGEMENT

The authors thank Science Foundation Ireland (03/IBN/B352) and the Higher Education Authority's Programme for Research in Third Level Institutions for funding. This work was presented (in part) at the European Young Investigators Workshop on “Carbohydrate Chemistry: From Synthesis to Applications” in Lyon, April 11–15, 2011.

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Related Research Data

1-O-Benzyl-2,3-O-iso­propyl­idene-6-O-tosyl-α-l-sorbo­furan­ose
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