Journal of Organic Chemistry 2011-12-02

Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates.

Yuyong Ma, Zhongzhen Li, Hefang Shi, Jian Zhang, Biao Yu

Index: J. Org. Chem. 76 , 9748, (2011)

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Abstract

Digitoxin, a clinically important cardiac trisaccharide, was assembled efficiently from digitoxigenin and 3,4-di-O-tert-butyldiphenylsilyl-d-digitoxosyl o-cyclopropylethynylbenzoate in 9 steps and 52% overall yield via alternate glycosylation and protecting group manipulation. The present synthesis showcases the advantage of the gold(I)-catalyzed glycosylation protocol in the synthesis of glycoconjugates containing acid-labile 2-deoxysugar linkages.© 2011 American Chemical Society