An unexpected sialylation: Total syntheses of GM4 and a positional isomer

Jacquelyn Gervay-Hague, John M. Peterson, Takeshi Oriyama, Samuel J. Danishefsky

Research output: Contribution to journalArticle

42 Scopus citations

Abstract

The use of glycals 3 and 4 as precursors to 1,2-anhydrosugars greatly simplifies the installation of a β-linked ceramide glycoside. By permuting the introduction of the ceramide and the sialic acid, one can access the ganglioside GM4 (1) and, by an unexpected regioselective glycosylation, its NeuAc (2→2) Gal positional isomer 10.

Original languageEnglish (US)
Pages (from-to)5465-5468
Number of pages4
JournalJournal of Organic Chemistry
Volume58
Issue number20
StatePublished - 1993
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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    Gervay-Hague, J., Peterson, J. M., Oriyama, T., & Danishefsky, S. J. (1993). An unexpected sialylation: Total syntheses of GM4 and a positional isomer. Journal of Organic Chemistry, 58(20), 5465-5468.