An Unexpected Sialylation: Total Syntheses of GM4 and a Positional Isomer

DOI: 10.1021/jo00072a031

Source and publish data:

Journal of Organic Chemistry p. 5465 - 5468 (1993)

Update date:2022-08-24

Topics:

Authors:

Gervay, Jacquelyn

Peterson, John M.

Oriyama, Takeshi

Danishefsky, Samuel J.

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Article abstract of DOI:10.1021/jo00072a031

The use of glycals 3 and 4 as precursors to 1,2-ahhydrosugars 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.

Full text of DOI:10.1021/jo00072a031

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