TY - JOUR
T1 - An unexpected sialylation
T2 - Total syntheses of GM4 and a positional isomer
AU - Gervay-Hague, Jacquelyn
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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M3 - Article
AN - SCOPUS:0027427655
VL - 58
SP - 5465
EP - 5468
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 20
ER -