Abstract
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...
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