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Indium trichloride promoted stereoselective synthesis of O-glycosides from trialkyl orthoformates

✍ Scribed by Debaraj Mukherjee; Syed Khalid Yousuf; Subhash C. Taneja

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 201 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.05.130

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✦ Synopsis

A novel, highly stereoselective method for O-glycosylation of glycals and glycosylbromides is developed using orthoformates as acceptors in the presence of InCl 3 to afford the corresponding O-glycopyranosides in 66-94% yield. Both perbenzyl and peracetyl glycals afford the corresponding 2,3-unsaturated-O-glycosides with high a-selectivity. Stoichiometric amounts of orthoformates are sufficient to bring about this transformation instead of large excesses of alcohols.

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