Stereoselective synthesis of a C-linked neuraminic acid disaccharide: potential building block for the synthesis of C-analogues of polysialic acids.
C-linked neuraminic acid disaccharide was synthesized in a diastereoselective manner from a sulfone donor and aldehyde acceptor, which was protected as a 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.
Kim
Jin-Hwan
JH
Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New York 12180, USA.
Huang
Fei
F
Ly
Mellisa
M
Linhardt
Robert J
RJ
D000447:Aldehydes / Q000737:chemistry; D002236:Carbohydrate Conformation; D002625:Chemistry, Organic / Q000379:methods*; D004187:Disaccharides / Q000737:chemistry; D015195:Drug Design; D008956:Models, Chemical; D009438:Neuraminic Acids / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D010782:Photolysis; D012794:Sialic Acids / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry
D000447:Aldehydes; D004187:Disaccharides; D009438:Neuraminic Acids; D012794:Sialic Acids; D013450:Sulfones; C021319:polysialic acid; D010100:Oxygen