%0 Journal Article %J Tetrahedron Letters %D 2007 %T Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides %A Sureshkumar, Gopalsamy %A Hotha, Srinivas %X

Propargyl 1,2-orthoesters are identified as glycosyl donors. Various glycosides and disaccharides were synthesized in a stereoselective manner using AuBr3 as the promoter. AuBr3 may activate the alkyne resulting in the formation of a 1,2-dioxolenium ion and also behaves as a Lewis acid to facilitate the attack of the glycosyl acceptor. The versatility of the protocol was demonstrated using a panel of aglycones comprising aliphatic, alicyclic, steroidal and sugar alcohols. (C) 2007 Elsevier Ltd. All rights reserved.

%B Tetrahedron Letters %I PERGAMON-ELSEVIER SCIENCE LTD %C THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND %V 48 %P 6564-6568 %8 SEP %G eng %N 37 %9 Article %3 Foreign %4 2.347 %R 10.1016/j.tetlet.2007.07.015