| 窦倩,张伟,闫鹏,刘志玲.化学通报,2018,81(8):720-726. |
| 熊去氧胆酸的合成 |
| Synthesis of Ursodeoxycholic Acid |
| 投稿时间：2018-03-13 修订日期：2018-04-13 |
| DOI： |
| 中文关键词: 甾族化合物 熊去氧胆酸 全合成 临界胶束浓度 |
| 英文关键词:Steroid,Ursodeoxycholic acid,Total synthesis,Critical micelle concentration |
| 基金项目: |
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| 摘要点击次数: 2340 |
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| 中文摘要: |
| 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还原来反应缩短路线，总产率达到28.8%。其结构经1H NMR、13C NMR和HRMS确认。其次，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。 |
| 英文摘要: |
| 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. |
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