A tandem Ferrier and Click reaction: a facile synthesis of triazolyl-2,3-dideoxypyranosides

Glycosyl azides, prepared in situ from glucal and trimethylsilyl azide via Ferrier rearrangement, undergo smooth coupling with alkynes under neutral conditions by means of 'Click reactions' to furnish 1,2,3-triazole-linked glycoconjugates in high yields and with moderate stereoselectivity. The method provides a convenient route to prepare glycoconjugates from glucals, trimethylsilyl azide, and alkynes via a three component reaction. (C) 2008 Published by Elsevier Ltd.