A versatile synthesis of the lactoneo-series antigens synthesis of sialyl dimer Lewis X and of dimer Lewis Y

Article abstract of DOI:10.1016/S0040-4039(97)00006-3

Readily available fucosyl α(1-3)azidoglucose disaccharide 6 is transformed with galactosyl donors 7 and 8 into Lewis X trisaccharide building blocks 9 and 12, respectively, in high yield. Their suitability for the construction of the lactoneo-series glycosphingolipids is demonstrated. For instance, 9 readily affords glycosyl donor 10 and acceptor 11, which permits the required regioselective 3-O-sialylation of the galactose moiety. Thus, from 11 and 12 hexasaccharide 14 is generated which afforded with lactase acceptor 17 the decisive octasaccharide intermediate Is which is then transformed either into sialyl dimer Lewis X (1) or into dimeric Lewis Y (2).