Synthesis of simple sea cucumber ganglioside analogs

Two simple sea cucumber ganglioside analogs 8 (NeuAcα2→6 Glcβ 1→1 docosanol) and 9 (NeuAcβ2→6 Glcβ 1→1 docosanol), containing a long-chain alcohol as a mimic of ceramide, have been synthesized. Coupling of the methyl 2-thioglycoside derivative of N-acetylneuraminic acid S with docosyl glucoside derivative 3 afforded the protected ganglioside analogs 6 and 7, which were deprotected to give the corresponding ganglioside analogs 8 and 9, respectively. The ¹³C-NMR data obtained for these anomers 8 and 9 should prove useful for the determination of anomeric configurations of sialic acid residues in gangliosides.