Direct C-glycosylation by indium-mediated alkynylation on sugar anomeric position.
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.
Lubin-Germain
Nadège
N
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
Baltaze
Jean-Pierre
JP
Coste
Alexis
A
Hallonet
Agnès
A
Lauréano
Hugo
H
Legrave
Grégory
G
Uziel
Jacques
J
Augé
Jacques
J
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
D004187:Disaccharides; D005663:Furans; D006027:Glycosides; D007204:Indium