Synthetic Studies on Sialoglycoconjugates 46: A Facile Total Synthesis of Ganglioside GD3

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Abstract
Sialic acids are well known as constituents of cell membrane-glycoconjugates and involved in their various biological functions. As far as we know, sialic acids are linked in an a-configuration at C-3 and C-6 of the Gal unit, at C-6 of the GlcNAc and GalNAc units and at C-8 of the sialic acid residue in sialoglycoconjugates. We have developed24 a facile a-stereoselective glycosylation of sialic acids by using 2-thioglycosides of sialic acids as glycosyl donors with suitably protected acceptors, using dimethyl(methy1thio)sulfonium triflate (DMTST) or N-iodosuccinimide(N1S)-mfluoromethanesulfonic acid (or TMS mflate) as the glycosidation promoter in acetonitrile. A variety of gangliosides5 and their analogs6.7 have been synthesized in this way. As a part of our continuing studies on the systematic synthesis and structure-function relationship of gangliosides in connection with a novel approach for the systematic synthesis of polysialoglycolipids, we describe here a facile stereocontrolled synthesis of ganglioside GD3 containing an a-sialyl-(2+8)-sialic acid residue in the molecule. Ganglioside GD3 is well known as human melanoma associated antigen9 and widely present in normal and pathogenic tissues. This ganglioside was first synthesized by Ogawa er ul in multiple steps.

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