Abstract
Two strategies were considered for the synthesis of 2,3-unsaturated O -glucosyl-1,2,3-triazoles. The first, involving reaction between tri-O -acetyl-d -glucal and triazole alcohols gave no stereoselectivity. A second strategy provided 2,3-unsaturated O -glycosides from glycals and alkynols through a Ferrier rearrangement; this method, employing montmorillonite K-10 doped with iron(III) chloride hexahydrate in dichloromethane afforded new glycosides in good to excellent yields within short times and with high α-stereoselectivities. Subsequently, the glucosides were coupled with 2-azido-1,4-naphthoquinone to produce a new series of 1,2,3-1H -triazolyl O -glucoside derivatives through a click reaction.
Key words rearrangements - triazoles - glycosides - alkynes - copper - click reactions
