Ganglioside GM4 (1) and GM3 (2) analogs, which contain mimics of the ceramide moieties of gangliosides, were synthesized. The syntheses of 1 and 2 feature stereoselective glycosylation of methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-beta-D- galacto-2-nonulopyranosid)onate (10) as the sialosyl donor with suitably protected galactose and lactose acceptors catalyzed by N-bromosuccinimide (NBS), iodine, and tetrabutylammonium trifluoromethanesulfonate (TBAOTf) as the glycosyl promoter in acetonitrile under kinetically controlled conditions. Compound 2 exhibited binding activity towards influenza virus A.