24-亚甲基-胆甾-3β,5α,6β-三醇的合成  

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

作　　者：张琪[1] 徐长荣[1] 周向东[1] 

机构地区：[1]第三军医大学医学检验系暨药学院药物化学教研室,重庆400038

出　　处：《第三军医大学学报》2009年第10期906-909,共4页Journal of Third Military Medical University

基　　金：重庆市自然科学基金(2007BB5053)~~

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,△5-3β-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、1HNMR、13CNMR、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。Objective To synthesize 24-methyleneeholestan-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 （^1HNMR）, carbon magnetic resonance spectroscopy, （^13CNMR） and infl-ared 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.

关 键 词：猪去氧胆酸 24-亚甲基-胆甾烷-3β 5α 6β-三醇 异丙基化 

分 类 号：R914.5[医药卫生—药物化学] R962[医药卫生—药学]