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目的利用化学方法高效合成PI-88糖基片段a-(1→2)-甘露糖三糖。方法以4,6位苯亚甲基保护的D-甘露糖硫苷3为原料合成N-对甲苯磺酰亚胺酯供体6,以TMSOTf作为促进剂,供体6与受体3进行糖苷化反应,得到a-(1→2)甘露糖二糖7,然后将二糖脱除苯甲酰基,再次与供体6进行糖苷化反应,合成出糖基片段a-(1→2)甘露糖三糖2。结果以85%和79%的糖苷化反应产率,得到a-(1→2)甘露糖二糖7和三糖2,为PI-88构效关系的研究提供物质基础和保障。
OBJECTIVE To efficiently synthesize a- (1 → 2) -mannose trisaccharide from the PI-88 glycosyl moiety by chemical methods. Methods D-mannosyl glucosinolate 3 protected by 4,6-position benzylidene was used as starting material to synthesize N-p-toluenesulfonylimide donor 6, TMSOTf as promoter, donor 6 and acceptor 3 (1 → 2) mannose disaccharide 7, and then the disaccharide to remove benzoyl, and again with the donor 6 glycosidation reaction, synthesis of sugar-based fragments of a- (1 → 2) mannose Sugar trisaccharide 2. Results A - (1 → 2) mannose disaccharide 7 and trisaccharide 2 were obtained at yields of 85% and 79%, respectively, which provided the material basis and guarantee for the structure-activity relationship of PI-88.