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  • Title: Efficient synthesis of a sialic acid alpha(2-->3)galactose building block and its application to the synthesis of ganglioside GM3.
    Author: Liu Y, Ruan X, Li X, Li Y.
    Journal: J Org Chem; 2008 Jun 06; 73(11):4287-90. PubMed ID: 18433175.
    Abstract:
    Glycosylation of various galactose derivatives with O-acetylated sialic acid N-phenyltrifluoroacetimidate as the donor was investigated. Efficient alpha(2,3)sialylation of galactose, with up to 73% yield and 8.4:1 stereoselectivity, was realized when 2,3,4-unprotected galactose derivatives and TBSOTf were used as acceptors and promoter, respectively. Sialylation of 2-(trimethylsilyl)ethyl 6-O-tert-butyldiphenylsilyl-beta-D-galactopyranoside (3f) gave the best result, and the resultant Neu5Ac alpha(2-->3)Gal disaccharide was successfully used in the synthesis of ganglioside GM3.
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