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 › peer-review

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

Cite this

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title = "An unexpected sialylation: Total syntheses of GM4 and a positional isomer",

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.",

author = "Jacquelyn Gervay-Hague and Peterson, {John M.} and Takeshi Oriyama and Danishefsky, {Samuel J.}",

year = "1993",

language = "English (US)",

volume = "58",

pages = "5465--5468",

journal = "Journal of Organic Chemistry",

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AU - Peterson, John M.

AU - Oriyama, Takeshi

AU - Danishefsky, Samuel J.

PY - 1993

Y1 - 1993

N2 - 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.

AB - 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.

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AN - SCOPUS:0027427655

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

Abstract

ASJC Scopus subject areas

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