摘要
以5-溴-2-氯-4′-乙氧基二苯甲烷为原料,与2,3-二-O-叔丁基二甲基硅基-5,6-O-异亚丙基-D-葡糖醛酸-1,4-内酯缩合后,再经还原、脱保护、酯化及水解反应合成了达格列净呋喃环杂质——(1S)-1,4-脱水-1-(4-氯-3-(4-乙氧基苄基)苯基)-D-葡萄糖,总收率29.0%,纯度98.5%,其结构经^1H NMR,^13C NMR,DEPT135,^1H-^1H COSY,HSQC,HMBC和MS(ESI)确证。
The furanose impurity of dapagliflozin,(1 S )-1,4-anhydro-1-[4-chloro-3-(4-ethoxy benzyl)phenyl]-D-glucitol, was synthesized by a five-step route of condensation, reduction and deprotection, esterification, hydrolysis, using 5-bromo-2-chloro-4′-ethoxydiphenylmethane and 2,3-di- O -tert-butyl dimethylsilyl-5,6- O -isopropylidene-D-glucono-1,4-lactone as starting materials with an overall yield of 29.0% and purity of 98.5%. The structure was confirmed by ^1 H NMR,^13 C NMR, DEPT135,^1 H-^1 H COSY , HSQC, HMBC and ESI-MS.
作者
罗海荣
顾荣领
王蓉
吴高鑫
LUO Hai-rong;GU Rong-ling;WANG Rong;WU Gao-xin(School of Material and Chemical Engineering,Tongren University 554300,China;Zhejiang Hisunpharm Co.,Ltd.,Taizhou 318000,China)
出处
《合成化学》
CAS
北大核心
2019年第7期563-567,共5页
Chinese Journal of Synthetic Chemistry
基金
贵州省科技合作计划项目(黔科合LH字[2016]7309号)
贵州省普通高等学校工程研究中心建设项目(黔教合KY字[2017]024)
铜仁学院博士科研启动基金资助项目(trxyD H1605)
