950665-05-1Relevant academic research and scientific papers
Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives
Bai, Yajun,Zhang, Qunzheng,Jia, Pu,Yang, Lingjian,Sun, Yuhong,Nan, Yefei,Wang, Shixiang,Meng, Xue,Wu, Yizhen,Qin, Fanggang,Sun, Zhe,Gao, Xiaokang,Liu, Pei,Luo, Kai,Zhang, Yajun,Zhao, Xinfeng,Xiao, Chaoni,Liao, Sha,Liu, Jianli,Wang, Cuiling,Fang, Jiacheng,Wang, Xiaoxiao,Wang, Jing,Gao, Rong,An, Xuexia,Zhang, Xunli,Zheng, Xiaohui
, p. 1667 - 1673 (2015/02/18)
A pilot-scale process has been developed for green and scalable synthesis of (±)-β-(3,4-dihydroxyphenyl) lactic acid ((±)-DSS) and their two important derivatives, namely, (±)-IDHP [(±)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate] and (±)-DBZ [(±)-bornyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate]. Subsequent hydrogenation has been carried out by employing Raney Ni as catalyst. The improved process results in higher yields of 47.5% for (±)-DBZ and 49.2% for (±)-IDHP compared to the initial process with a yield of 12% for (±)-DBZ and 18% for (±)-IDHP in our original medicinal chemistry route. Furthermore, kilograms of optical DBZ [(-)-S-DBZ and (+)-R-DBZ, >99% ee] and IDHP [(-)-S-IDHP and (+)-R-IDHP, >99% ee] have been produced by chiral high-performance liquid chromatography in good yield (>84%).
Efficient and practical asymmetric synthesis of isopropyl (R)-3-(3′,4′-dihydroxyphenyl)-2-hydroxypropanoate and its enantiomer
Chen, Ming,Chen, Hui,Wang, Yuzhen,Wang, Haibo,Nan, Yefei,Zheng, Xiaohui,Jiang, Ru
, p. 4 - 7 (2011/04/17)
The highly enantioselective synthesis of (R)-isopropyl 3-(3′, 4′-dihydroxyphenyl)-2-hydroxypropanoate and its enantiomer has been achieved starting from 3,4-dihydroxybenzaldehyde. The stereogenic centers were established through asymmetric dihydroxylation of (E)-isopropyl 3,4-bis(benzyloxy) cinnamate. A convenient manipulation in selective catalytic hydrogenation and deprotection was also accomplished in HCl-iPrOH employing 10% Pd/C catalyst.
