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- W1967665391 abstract "Abstract As more and more biological functions1-10 of gangliosides are being revealed, their facile, stereocontrolled synthesis is strongly required. We have developed11-l4 an α-stereoselective glycosylation of sialic acids, α-sialyl-(2→8)-sialic acid and α-sialyl-(2→8)-α-sialyl-(2→8)-sialic acid, by using their 2-thioglycosides as the glycosyl donor and suitably protected acceptors, and dimethyl(methy1thio)sulfonium triflate (DMTST) or N-iodosuccinimide (NIS)-trifluoromethanesufonic acid (or TMS triflate) as the glycosyl promoter in acetonitrile. In this way, we have synthesized a variety of gangliosides15 and their analogs.16 Previously,13 we synthesized Ganglioside GD3 containing α-sialyl-(2-8)-sialic acid residue in the molecule, in connection with a novel approach for systematic synthesis of polysialo-glycoconjugates. As a part of our continuing studies on the synthesis and elucidation of the functions of gangliosides, we describe here a facile, stereocontrolled, total synthesis of ganglioside GD2. Ganglioside GD2, which was first isolated from human brain by R. Kuhn et al.,17 is well known as a human melanoma associated antigen.18" @default.
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- W1967665391 date "1993-12-01" @default.
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- W1967665391 title "Synthetic Studies on Sialoglycoconjugates 50: Total Synthesis of Ganglioside GD2" @default.
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- W1967665391 doi "https://doi.org/10.1080/07328309308020129" @default.
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