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 journal › Article

41 Citations (Scopus)

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

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Ceramides
Isomers
Glycosylation
N-Acetylneuraminic Acid
Glycosides
ganglioside GM4-1

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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.

An unexpected sialylation : Total syntheses of GM4 and a positional isomer. / Gervay-Hague, Jacquelyn; Peterson, John M.; Oriyama, Takeshi; Danishefsky, Samuel J.

In: Journal of Organic Chemistry, Vol. 58, No. 20, 1993, p. 5465-5468.

Research output: Contribution to journal › Article

Gervay-Hague, J, Peterson, JM, Oriyama, T & Danishefsky, SJ 1993, 'An unexpected sialylation: Total syntheses of GM4 and a positional isomer', Journal of Organic Chemistry, vol. 58, no. 20, pp. 5465-5468.
Gervay-Hague J, Peterson JM, Oriyama T, Danishefsky SJ. An unexpected sialylation: Total syntheses of GM4 and a positional isomer. Journal of Organic Chemistry. 1993;58(20):5465-5468.
Gervay-Hague, Jacquelyn ; Peterson, John M. ; Oriyama, Takeshi ; Danishefsky, Samuel J. / An unexpected sialylation : Total syntheses of GM4 and a positional isomer. In: Journal of Organic Chemistry. 1993 ; Vol. 58, No. 20. pp. 5465-5468.
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