Studies in C-glycoside synthesis: from SN2-like displacement to cross coupling

C-glycosides are hydrolytically stable analogs of glycans and glycoconjugates which in some cases have improved pharmacokinetic properties compared to their O-linked counterparts. While many approaches to specific C-glycosides have been described, general methods for C-linked disaccharide production are comparatively rare. This talk describes our labs studies directed to developing methods for C-linked disaccharide synthesis, including S_N2 displacement of glycosyl sulfonates with carbon nucleophiles and light-free Ni-mediated cross-coupling reactions with redox active esters. The scope and limitations of these chemistries as well as the elaboration of the resulting products into C-linked disaccharides will be discussed.