Synthesis of 24-methylenecholestan-3β,5α,6β-triol

张琪; 徐长荣; 周向东

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Synthesis of 24-methylenecholestan-3β,5α,6β-triol

更新时间：2026-01-09

- Synthesis of 24-methylenecholestan-3β,5α,6β-triol
- Journal of Army Medical University Vol. 31, Issue 10, Pages: 906-909(2009)
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  CLC： R914.5;R962
- Published：2009
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张琪,徐长荣,周向东.24-亚甲基-胆甾-3β,5α,6β-三醇的合成[J].陆军军医大学学报(原第三军医大学学报),2009,31(10):906-909.

　ZHANG Qi,XU Chang-rong,ZHOU Xiang-dong.Synthesis of 24-methylenecholestan-3β,5α,6β-triol[J].J Amry Med Univ (J Third Mil Med Univ),2009,31(10):906-909.
张琪,徐长荣,周向东.24-亚甲基-胆甾-3β,5α,6β-三醇的合成[J].陆军军医大学学报(原第三军医大学学报),2009,31(10):906-909. DOI：

　ZHANG Qi,XU Chang-rong,ZHOU Xiang-dong.Synthesis of 24-methylenecholestan-3β,5α,6β-triol[J].J Amry Med Univ (J Third Mil Med Univ),2009,31(10):906-909. DOI：

摘要

目的高效合成海洋天然产物24-亚甲基-胆甾烷-3β

5α

6β-三醇。方法以猪去氧胆酸为原料，△

-3β-四氢吡喃氧基胆甾-24-酮为关键中间体，格氏试剂异丙基化为关键步骤，经7步反应合成目标分子。结果以53%的总收率合成目标分子，其结构为MS、

HNMR、

CNMR、IR所证实。结论以本法合成24-亚甲基-胆甾烷-3β，5α，6β-三醇，原料廉价易得、路线简短、收率高、符合原子经济性。

Abstract

Objective To synthesize 24-methylenecholestan-3β

5α

6β-triol

a compound same as a marine natural product

. Methods The target molecule was synthesized in 7 steps using hyodeoxycholic acid as the starting material

3β-(tetrahydropyran-2-yloxy)-cholest-5-ene-24-ketone as the key intermediate and isopropylation in Grignard reagents as the key step. Results The target molecule was synthesized in a total yield of 53% and confirmed by mass spectrometry (MS)

proton magnetic resonance spectroscopy (

HNMR)

carbon magnetic resonance spectroscopy

(

CNMR) and infrared spectroscopy (IR). Conclusion Our method to synthesize 24-methylene-cholestan-3β

5α

6β-triol is characterized by easily available and cheap starting material

short synthetic route

high yield and atom-economic.

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