ol101625p_si_001.pdf (4.76 MB)
A Pd-Catalyzed Approach to (1→6)-Linked C-Glycosides
journal contribution
posted on 2010-09-03, 00:00 authored by Dennis C. Koester, Markus Leibeling, Roman Neufeld, Daniel B. WerzA 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 α- or the β-derivative, depending on the hydride source.