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

J Gervay, JM Peterson, T Oriyama…

Index: Gervay, Jacquelyn; Peterson, John M.; Oriyama, Takeshi; Danishefsky, Samuel J. Journal of Organic Chemistry, 1993 , vol. 58, # 20 p. 5465 - 5468

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Citation Number: 38

Abstract

The use of glycals 3 and 4 as precursors to 1, 2-anhydrosugars greatly simplifies the installation of a 8-linked ceramide glycoside. By permuting the introduction of the ceramide and the sialic acid, one can access the ganglioside GM~(1) and, by an unexpected regioselective glycosylation, ita NeuAc (2+ 2) Gal positional isomer 10.