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1. Stereoselective synthesis of a C-linked neuraminic acid disaccharide: potential building block for the synthesis of C-analogues of polysialic acids

Author

Jin-Hwan Kim, Fei Huang, Ly, Mellisa, and Linhardt, Robert J.

Subjects
Aldehydes -- Chemical properties, Sugars -- Chemical properties, Samarium -- Chemical properties, Stereochemistry -- Analysis, Sulfones -- Chemical properties, Biological sciences, Chemistry
Abstract

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

Published
2008

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