氨基和羟基双保护葡萄糖苷关键中间体的合成  

Synthesis of the a intermediate of amino and hydroxyl group double protected glucoside

作　　者：杨涛 杨劲松[1] YANG Tao;YANG Jinsong(West China School of Pharmacy,Sichuan University,Chengdu,Sichuan,610041 P.R.China)

机构地区：[1]四川大学华西药学院,四川成都610041

出　　处：《华西药学杂志》2022年第6期605-607,共3页West China Journal of Pharmaceutical Sciences

基　　金：国家自然科学基金资助项目(批准号:21772132)。

摘　　要：目的合成并优化1-O-叔丁基二苯基硅烷基-2-去氧-4,6-O-苯亚甲基-2-(2,2,2-三氯乙氧羰酰胺)-β-D-吡喃葡萄糖苷。方法以2-氨基-2-去氧-D-葡萄糖盐酸盐为原料,经过2位氨基酰化、端基羟基硅基化、4,6位羟基苯亚甲基化等6步反应,得到目标化合物Ⅰ。目标化合物经~^(1)HNMR、^(13)CNMR及LC-MS(ESI)验证结构。结果制得目标化合物Ⅰ的总收率为64.1%。结论经过优化的合成路线比文献的提高了合成效率。OBJECTIVE To optimize the synthesis process of 1-O-tert-butyldiphenylsilyl-2-deoxy-4,6-O-phenylmethyl-2-(2,2,2-trichloroethoxycarbonamide)-β-D-glucopyranose.METHODS 2-amino-2-deoxy-D-glucose hydrochloride was used as raw material,and the target compound was synthesized and identified by^(1)HNMR,^(13)CNMR and LC-MS(ESI)through a six-step reaction of 2-amino-acylation,terminal hydroxy-silylation and 4,6-hydroxy-benzene-methylation.RESULTS CompoundⅠwas synthesized with a total yield of 64.1%.CONCLUSION The optimized synthesis route improves the synthesis efficiency compared with the reported synthesis route.

关 键 词：双保护葡糖糖苷 关键中间体 基团保护 单磷酰脂质A 叔丁基二苯基硅烷基 2-去氧吡喃葡萄糖 合成优化 2 2 2-三氯乙氧羰酰基 

分 类 号：R914[医药卫生—药物化学]