Stereoselective Synthesis of a C-linked Neuraminic Acid Disaccharide: Potential Building Block for the Synthesis of C-Analogs of Polysialic Acids

Abstract

C-Linked neuraminic acid disaccharide was synthesized in a diastereoselective manner from a sulfone donor and aldehyde acceptor, which was protected as propargyl ether, through a samarium mediated coupling reaction. The resulting disaccharide has acetal and phenyl sulfide functional groups that can be easily converted into aldehyde and phenyl sulfone groups by photolysis and oxidation reactions, to serve as disaccharide acceptor and donor, respectively.