Synthesis of carbapenem skeleton
10.13220/j.cnki.jipr.2017.12.012
- VernacularTitle:碳青霉烯骨架的合成研究
- Author:
Ying WANG
1
;
Heng ZHANG
;
Wei WU
;
Yi-Hong YANG
;
Xing-Wang WANG
Author Information
1. 武汉工程大学化工与制药学院
- Keywords:
carbapenem skeleton;
carbapenem antibiotics;
synthesis
- From:
Journal of International Pharmaceutical Research
2017;44(12):1145-1149
- CountryChina
- Language:Chinese
-
Abstract:
Objective To investigete a new synthetic route for carbapenem skeleton(1)for industrial production. Methods (3S,4R)-4-acetoxy-3-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one(4-AA)was used as raw material,and 1 was obtained from it through a homemade chiral auxiliary zinc powder catalyzed Reformatsky reaction,hydrolysis,the introduction of β-carboxyl es?ter structure,deprotection,cyclization,and activation by diphenyl chlorophosphate. The each key process was optimized,and the structures of intermediate and target compounds were confirmed by MS,GC-MS and 1H NMR.Results and Conclusion The total yield was 19.9%.The improved process conditions are mild,easy to operate,and suitable for industrial production.
