Synthesis of a thio-linked analogue of sialyl Lewis X

Article abstract of DOI:10.1016/0040-4039(96)00061-5

Thiolinked sialyl Lewis X analogue 2 was obtained from neuraminic acid, D-galactose, and L-fucose. Galactose was transformed into 3-thiogalactose building block 6 and also into the required 3,4-dithioglucose moiety. Thioglycoside bond formation was performed via base-promoted S-glycosylation [Neu5Acα(2-3S)Gal and Galβ(1-4S)Glc linkages] and via acid catalyzed S-glycosylation [Fucα(1-3S)Glc and Glcβ-(1-1S)heptyl linkages].