title: A Pd-catalyzed approach to (1-->6)-linked C-glycosides.
abstract: A flexible and robust method for the assembly of (1-->6)-linked C-glycosidic disaccharides is presented. The key reaction is a Pd-catalyzed coupling of 1-iodo- or 1-triflato-glycals with alkynyl glycosides. Reinstallation of the native hydroxyl group pattern is achieved after selective hydrogenation of the triple bond using Raney-nickel. Epoxidation with DMDO and reductive epoxide opening gives access to either the alpha- or the beta-derivative, depending on the hydride source.
authors.affiliation: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Gottingen, Tammannstr. 2, D-37077 Göttingen, Germany.
authors.forename: Dennis C
authors.initials: DC
authors.lastname: Koester
authors.forename: Markus
authors.initials: M
authors.lastname: Leibeling
authors.forename: Roman
authors.initials: R
authors.lastname: Neufeld
authors.forename: Daniel B
authors.initials: DB
authors.lastname: Werz
mesh_terms: D002384:Catalysis; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D004187:Disaccharides; D004852:Epoxy Compounds; D006027:Glycosides; D010165:Palladium