title: Direct C-glycosylation by indium-mediated alkynylation on sugar anomeric position.
abstract: Indium-mediated alkynylation reaction was studied for the direct preparation of C-glycosides. Easily available starting sugar derivatives with an acetyl group at the anomeric position were tested as electrophiles toward alkynylindium reagents under Barbier conditions. Good yields and stereoselectivities were observed during the reaction. The alkynylation was applied to the synthesis of an alpha-(1-->6)-C-disaccharide analogue of isomaltoside.
authors.affiliation: Laboratoire de Synthèse Organique Sélective et Chimie Organométallique, Unité CNRS-UCP-ESCOM 8123, 5 mail Gay-Lussac, Neuville-sur-Oise, 95031 Cergy-Pontoise, France. nadege.lubin-germain@u-cergy.fr
authors.forename: Nadège
authors.initials: N
authors.lastname: Lubin-Germain
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Baltaze
authors.forename: Alexis
authors.initials: A
authors.lastname: Coste
authors.forename: Agnès
authors.initials: A
authors.lastname: Hallonet
authors.forename: Hugo
authors.initials: H
authors.lastname: Lauréano
authors.forename: Grégory
authors.initials: G
authors.lastname: Legrave
authors.forename: Jacques
authors.initials: J
authors.lastname: Uziel
authors.forename: Jacques
authors.initials: J
authors.lastname: Augé
mesh_terms: D020650:Combinatorial Chemistry Techniques; D004187:Disaccharides; D005663:Furans / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007204:Indium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004187:Disaccharides; D005663:Furans; D006027:Glycosides; D007204:Indium