Zhiyuan Z, Magnusson G
Chemical Center, Lund Institute of Technology, University of Lund, Sweden.
Carbohydr Res. 1994 Sep 1;262(1):79-101. doi: 10.1016/0008-6215(94)84006-7.
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.
2-（三甲基硅基）乙基（Me3SiCH2CH2）2,3,6-三-O-苯甲酰基-4-O-（2,3-二-O-苯甲酰基-6-O-对甲氧基苄基-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖苷）与不同的2-、3-、4-或6-“脱氧-D-半乳糖”衍生物进行糖基化反应，得到相应的脱氧三糖。去除保护基团后得到Me3SiCH2CH2 2''-、3''-、4''-和6''-脱氧球三糖。通过半缩醛将保护的Me3SiCH2CH2球三糖转化为相应的三氯乙酰亚胺酯，总产率为91-96%。3-（十六烷基磺酰基-2-[十六烷基磺酰基）甲基]丙醇与三氯乙酰亚胺酯进行糖基化反应，然后去除保护基团，得到标题所示的新糖脂。
