熊去氧胆酸的合成

通过廉价易得的猪去氧胆酸为起始原料,以Shapiro反应为关键步骤,经酯化、选择性氧化、环氧化、脱保护等一系列反应成功合成了熊去氧胆酸,总产率为25.8%。在此基础上对该法进行了改良,使用硅基保护、Rubuttom氧化和Clemmensen还原来缩短反应路线,总产率达到28.8%。产物结构经1H NMR、13C NMR和HRMS确认。通过芘荧光探针法对结构相近的胆酸盐的聚集行为进行探究,可以推测临界胶束浓度只与结构中羟基的数量有关,而与羟基的构型没有直接联系。

Synthesis of Ursodeoxycholic Acid

Using cheaper and available HDCA (hyodeoxycholic acid) as the starting material, this route acquires 25.8% overall yield with Shapiro reaction as the critical step, esterification, selective oxidation, epoxidation and deprotection. The whole procedure was modified to make steps shorter with 28.8% total yield through silyl protection, Rubottom oxidation and Clemmensen reduction. The structures of all synthetic compounds were identified by HNMR, 13CNMR and HRMS. The aggregation behavior of similar bile acid salts with pyrene fluorescent probe was studied to show that critical micelle concentration (CMC) value was only related to the number of hydroxyl group instead of configuration.