Development of highly efficient and stereocontrolled O-glycosylation methodologies and its application to the construction of bacterial glycans

Abstract

Glycosylations have been used repeatedly as the key reaction in the synthesis of oligosaccharides and polysaccharides, therefore both of efficiency and stereoselectivity of the glycosylations are important. There has been reported the construction of 1,2-cis glycoside found in various bioactive glycoconjugate glycans from eukaryotes as well as prokaryotes, although a few for the definite methodologies to construct stereoselectively. Approaching from both efficiency and stereoselectivity of the reactions, we developed various highly efficient and stereocontrolled O-glycosylation methodologies for the construction of 1,2-cis glycosides. We also showed that their 1,2-cis glycosylation methodologies have been applied to the stereoselective synthesis of various bacterial glycoconjugate glycans. ©2009 FCCA (Forum: Carbohydrates Coming of Age).