Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 19, Issue 11, Pages 3093-3095Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2009.04.003
Keywords
Glycosylation; Ferrier rearrangement; alpha-Selectivity; 2,3-Unsaturated glycosides
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Funding
- Nanyang Technological University
- Ministry of Education, Singapore
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A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid. (S)-CSA acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could be coupled with glucal to give the desired pseudoglycosides in good to excellent yields with exclusive alpha-stereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.
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