Subba Reddy BV1, Praneeth K, Yadav JS.
Carbohydr Res. 2011 Jun 1;346(8):995-8. doi: 10.1016/j.carres.2010.12.015. Epub 2010 Dec 22.Glycosyl azides undergo smooth 1,3-dipolar cycloaddition with benzyne generated in situ from 2-(trimethylsilyl)phenyltrifluoromethanesulfonate and cesium fluoride under mild conditions to furnish 1,2,3-benzotriazole-linked glycoconjugates in excellent yields and with high stereoselectivity. This method provides a novel class of benzotriazole linked glycoconjugates in a single-step reaction. This is the first example of a fluoride- triggered 1,3-dipolar cycloaddition of benzyne with glycosyl azides.Copyright © 2010 Elsevier Ltd. All rights reserved.