Citation: Dou Qian, Yan Peng, Liu Zhiling, Zhang Wei. Synthesis of Ursodeoxycholic Acid[J]. Chemistry, ;2018, 81(8): 720-726. shu

Synthesis of Ursodeoxycholic Acid

Research Institute of Shanxi Yanchang Petroleum(Group) Co., Ltd, Xi'an 710075

Corresponding author: Zhang Wei, ycsy_zw@163.com
Received Date: 13 March 2018
Accepted Date: 17 April 2018

Figures(6)

Using inexpensive and readily available hyodeoxycholic acid (HDCA) as the starting material and with the Shapiro reaction as a key step, ursodeoxycholic acid was successfully synthesized by a series of reactions including esterification, selective oxidation, epoxidation, and deprotection. The total yield was 25.8%. The whole procedure was further modified to make steps shorter through silyl protection, Rubottom oxidation and Clemmensen reduction, with an overall yield of 28.8%. The structures of all synthetic compounds were identified by ¹H NMR, ¹³C NMR and HRMS. The aggregation behavior of similar bile acid salts with pyrene fluorescent probe was studied, the results showed that critical micelle concentration (CMC) value is only related to the number of hydroxyl group instead of configuration.
- Ursodeoxycholic acid,
- Critical micelle concentration
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沈阳化工大学材料科学与工程学院沈阳 110142