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

IR@CSIR-IIIM

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Title Indium trichloride promoted stereoselective synthesis of O-glycosides from trialkyl orthoformates
 
Creator Mukherjee, Debaraj
Yousuf, Syed Khalid
Taneja, Subhash C.
 
Subject Chemical Sciences
 
Description A novel, highly stereoselective method for O-glycosylation of glycals and glycosylbromides is developed using orthoformates as acceptors in the presence of InCl3 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.
 
Date 2008
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://iiim.csircentral.net/275/1/10.1016j.tetlet.2008.05.130.pdf
Mukherjee, Debaraj and Yousuf, Syed Khalid and Taneja, Subhash C. (2008) Indium trichloride promoted stereoselective synthesis of O-glycosides from trialkyl orthoformates. Tetrahedron Letters, 49 (33). pp. 4944-4948. ISSN 00404039
 
Relation http://dx.doi.org/10.1016/j.tetlet.2008.05.130
http://iiim.csircentral.net/275/