Synthesis of CH2-Linked α(1,6)-Disaccharide Analogues by α-Selective Radical Coupling C-Glycosylation

C-Linked carbohydrate structure, in which the cleavable O-glycosidic linkage is replaced by a carbon unit, is a useful tool for functional analyses of glycoconjugates. We describe a synthetic method for alpha-CH2-linked disaccharide structures, such as Glc(1,6)-Glc, by stereoselective radical-coupling C-glycosylation between a conformationally constrained and stable C1-sp(3) hybridized xanthate donor and a carefully designed acceptor.