Title of article
Indium trichloride promoted stereoselective synthesis of O-glycosides from trialkyl orthoformates
Author/Authors
Mukherjee، نويسنده , , Debaraj and Yousuf، نويسنده , , Syed Khalid and Taneja، نويسنده , , Subhash C.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2008
Pages
5
From page
4944
To page
4948
Abstract
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 α-selectivity. Stoichiometric amounts of orthoformates are sufficient to bring about this transformation instead of large excesses of alcohols.
Keywords
O-Glycosylation , Glycosyl halide , glycals , Trialkyl orthoformate , InCl3
Journal title
Tetrahedron Letters
Serial Year
2008
Journal title
Tetrahedron Letters
Record number
1860594
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