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

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

An unexpected sialylation: Total syntheses of G_M4 and a positional isomer

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

Research output: Contribution to journal › Article

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 G_M4 (1) and, by an unexpected regioselective glycosylation, its NeuAc (2→2) Gal positional isomer 10.

Original language	English (US)
Pages (from-to)	5465-5468
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	58
Issue number	20
State	Published - 1993
Externally published	Yes

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 G_M4 and a positional isomer. Journal of Organic Chemistry, 58(20), 5465-5468.

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