Synthesis of Double-Chain Bis-sulfone Neoglycolipids of the 2'-, 3'-, and 6'-Deoxyglobotrioses

Article abstract of DOI:10.1021/jo00127a042

Partially protected 2-(trimethylsilyl)ethyl deoxylactosides (deoxygenated in the 2-, 3-, and 6-positions of the galactose unit) were synthesized via various routes and glycosylated with galactosyl donors to give the corresponding deoxytrisaccharides.Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2'-, 3'-, and 6'-deoxyglobotriosides.Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in 86 - 96percent overall yield.Glycosylation of 3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propanol with the trisaccharidic trichloroacetimidates, in 37 - 68percent yield, followed by removal of protecting groups, gave the title neoglycolipids.