The University of Southampton
University of Southampton Institutional Repository

Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives

Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives
Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives
A pilot-scale process has been developed for green and scalable synthesis of (±)-?-(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%).
1667-1673
Bai, Yajun
8a1a6831-6811-4760-afec-66e0ab31dc88
Zhang, Qunzheng
64fded11-c4c3-4592-bade-7ef7ecbe7121
Jia, Pu
37dd65ff-a8f3-4e57-a69d-806457d874f5
Yang, Lingjian
8f65983a-d494-414a-9731-3f8573362883
Sun, Yuhong
3805c192-a52d-4028-b264-8ec7fe603214
Nan, Yefei
42a4adab-3f3f-430e-b981-fa552f6fff31
Wang, Shixiang
2be44e88-eb77-400c-89d1-1d03ae3119f1
Meng, Xue
c5327919-6c2b-4500-a101-17ab2bb524ca
Wu, Yizhen
cbb05337-72ac-4b39-bbe4-94b35151bdad
Qin, Fanggang
1358aefe-b422-437e-aec7-d87259492c9f
Sun, Zhe
743cc7be-e3c6-4810-9cea-8ad2a38ccefc
Gao, Xiaokang
e141e21d-d70a-4034-9161-37fe144c50f8
Liu, Pei
819ed33a-cef6-4a10-bc18-447df091f579
Luo, Kai
040f4edf-4936-4c71-8b23-85e6b9079aa8
Zhang, Yajun
1b7ad023-9838-46db-9be5-175fa92e025d
Zhao, Xinfeng
06658305-be04-4a95-b345-397c32aaceb6
Xiao, Chaoni
39c4ad2c-5a29-4443-8f2e-c79bcac819d5
Liao, Sha
054d7bbe-243b-4f39-b755-48d231a9a4a6
Liu, Jianli
635d8373-8520-4669-8578-f9688a8931f3
Wang, Cuiling
eebc0958-3945-4fd1-849b-39a42c81d97c
Fang, Jiacheng
5da41da2-8157-48dd-a331-87c56e9acd45
Wang, Xiaoxiao
954407e9-5586-4e8a-90f4-dc14e7d966f4
Wang, Jing
28dffdc1-cb6c-40da-b595-88dc7bc1cf1d
Gao, Rong
5767ce81-e322-4a3d-9cee-e0ab67f415b9
An, Xuexia
3a4657d7-678e-45fc-8915-2fc8fbc9a0d9
Zhang, Xunli
d7cf1181-3276-4da1-9150-e212b333abb1
Zheng, Xiaohui
a42fbf32-c855-4ae7-adc1-e56debcc1ecc
Bai, Yajun
8a1a6831-6811-4760-afec-66e0ab31dc88
Zhang, Qunzheng
64fded11-c4c3-4592-bade-7ef7ecbe7121
Jia, Pu
37dd65ff-a8f3-4e57-a69d-806457d874f5
Yang, Lingjian
8f65983a-d494-414a-9731-3f8573362883
Sun, Yuhong
3805c192-a52d-4028-b264-8ec7fe603214
Nan, Yefei
42a4adab-3f3f-430e-b981-fa552f6fff31
Wang, Shixiang
2be44e88-eb77-400c-89d1-1d03ae3119f1
Meng, Xue
c5327919-6c2b-4500-a101-17ab2bb524ca
Wu, Yizhen
cbb05337-72ac-4b39-bbe4-94b35151bdad
Qin, Fanggang
1358aefe-b422-437e-aec7-d87259492c9f
Sun, Zhe
743cc7be-e3c6-4810-9cea-8ad2a38ccefc
Gao, Xiaokang
e141e21d-d70a-4034-9161-37fe144c50f8
Liu, Pei
819ed33a-cef6-4a10-bc18-447df091f579
Luo, Kai
040f4edf-4936-4c71-8b23-85e6b9079aa8
Zhang, Yajun
1b7ad023-9838-46db-9be5-175fa92e025d
Zhao, Xinfeng
06658305-be04-4a95-b345-397c32aaceb6
Xiao, Chaoni
39c4ad2c-5a29-4443-8f2e-c79bcac819d5
Liao, Sha
054d7bbe-243b-4f39-b755-48d231a9a4a6
Liu, Jianli
635d8373-8520-4669-8578-f9688a8931f3
Wang, Cuiling
eebc0958-3945-4fd1-849b-39a42c81d97c
Fang, Jiacheng
5da41da2-8157-48dd-a331-87c56e9acd45
Wang, Xiaoxiao
954407e9-5586-4e8a-90f4-dc14e7d966f4
Wang, Jing
28dffdc1-cb6c-40da-b595-88dc7bc1cf1d
Gao, Rong
5767ce81-e322-4a3d-9cee-e0ab67f415b9
An, Xuexia
3a4657d7-678e-45fc-8915-2fc8fbc9a0d9
Zhang, Xunli
d7cf1181-3276-4da1-9150-e212b333abb1
Zheng, Xiaohui
a42fbf32-c855-4ae7-adc1-e56debcc1ecc

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 and Zheng, Xiaohui (2014) Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives. Organic Process Research & Development, 18 (12), 1667-1673. (doi:10.1021/op4002593).

Record type: Article

Abstract

A pilot-scale process has been developed for green and scalable synthesis of (±)-?-(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%).

Text
Pilot-Scale Synthesis of Danshensu OrgProResDev v18pp1667-1673 Bai14.pdf - Version of Record
Restricted to Repository staff only
Request a copy

More information

Published date: 26 November 2014
Organisations: Bioengineering Group

Identifiers

Local EPrints ID: 372871
URI: http://eprints.soton.ac.uk/id/eprint/372871
PURE UUID: 140b5cb3-735e-4a9f-9749-f3b9e60ddc46
ORCID for Xunli Zhang: ORCID iD orcid.org/0000-0002-4375-1571

Catalogue record

Date deposited: 24 Dec 2014 12:21
Last modified: 10 Dec 2019 01:42

Export record

Altmetrics

Contributors

Author: Yajun Bai
Author: Qunzheng Zhang
Author: Pu Jia
Author: Lingjian Yang
Author: Yuhong Sun
Author: Yefei Nan
Author: Shixiang Wang
Author: Xue Meng
Author: Yizhen Wu
Author: Fanggang Qin
Author: Zhe Sun
Author: Xiaokang Gao
Author: Pei Liu
Author: Kai Luo
Author: Yajun Zhang
Author: Xinfeng Zhao
Author: Chaoni Xiao
Author: Sha Liao
Author: Jianli Liu
Author: Cuiling Wang
Author: Jiacheng Fang
Author: Xiaoxiao Wang
Author: Jing Wang
Author: Rong Gao
Author: Xuexia An
Author: Xunli Zhang ORCID iD
Author: Xiaohui Zheng

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×