A Pd-catalyzed approach to (1-->6)-linked C-glycosides.
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.
Koester
Dennis C
DC
Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Gottingen, Tammannstr. 2, D-37077 Göttingen, Germany.
Leibeling
Markus
M
Neufeld
Roman
R
Werz
Daniel B
DB
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*
D004187:Disaccharides; D004852:Epoxy Compounds; D006027:Glycosides; D010165:Palladium