title: 1,3-Dipolar cycloaddition of sugar azides with benzyne: a novel synthesis of 1,2,3-benzotriazolyl glycoconjugates.
abstract: 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.
authors.affiliation: Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India. basireddy@iict.res.in
authors.forename: Basi V
authors.initials: BV
authors.lastname: Subba Reddy
authors.forename: Karanam
authors.initials: K
authors.lastname: Praneeth
authors.forename: Jhillu S
authors.initials: JS
authors.lastname: Yadav
mesh_terms: D001386:Azides / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D001386:Azides; D001555:Benzene Derivatives; D006001:Glycoconjugates; D014230:Triazoles; C524146:benzyne