Synthesis of double-chain bis-sulfone neoglycolipids of the 2''-, 3''-, 4''-, and 6''-deoxyglobotrioses.
2-(Trimethylsilyl)ethyl (Me3SiCH2CH2) 2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-benzoyl-6-O-p-methoxybenzyl-beta-D- galactopyranosyl-beta-D-glucopyranoside was glycosylated with different 2-, 3-, 4-, or 6-"deoxy-D-galactose" derivatives to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the Me3SiCH2CH2 2''-, 3''-, 4''-, and 6''-deoxyglobotriosides. Transformation of the protected Me3SiCH2CH2 globotriosides into the corresponding trichloroacetimidates proceeded, via the hemiacetals, in 91-96% over-all yield. Glycosylation of 3-(hexadecylsulfonyl-2-[hexadecylsulfonyl)methyl]propanol with the trichloroacetimidates, followed by removal of protecting groups, gave the title neoglycolipids.
Chemical Center, Lund Institute of Technology, University of Lund, Sweden.
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Zhiyuan
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Magnusson
D002240:Carbohydrate Sequence; D006017:Glycolipids / Q000138:chemical synthesis*; D006031:Glycosylation; D008969:Molecular Sequence Data; D013450:Sulfones / Q000138:chemical synthesis*; D014312:Trisaccharides / Q000138:chemical synthesis*
D006017:Glycolipids; D013450:Sulfones; D014312:Trisaccharides