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

Jin Hwan Kim, Fei Huang, Meilisa Ly, Robert J. Linhardt

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)9497-9500
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number23
DOIs
StatePublished - 5 Dec 2008
Externally publishedYes

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