岩藻甾醇的合成工艺研究  

Investigation on the Synthetic Process of Fucosterol

作　　者：李丙乾 孙彬[2] 金灿[1,2] LI Bingqian;SUN Bin;JIN Can(College of Pharmaceutical Sciences,Zhejiang University of Technology,Hangzhou 310014,China;Collaborative Innovation Centre of Yangtze River Delta Region Green Pharmaceuticals,Zhejiang University of Technology,Hangzhou 310014,China)

机构地区：[1]浙江工业大学药学院,浙江杭州310014 [2]浙江工业大学长三角绿色制药协同创新中心,浙江杭州310014

出　　处：《合成化学》2023年第11期882-888,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(22078299,22108250)。

摘　　要：岩藻甾醇(1)作为一种具有多种医药活性的植物甾醇,应用前景广阔,但岩藻甾醇天然来源少且提取率较低。本文设计并验证了一条以猪去氧胆酸(2)为起始原料,经甲酯化、磺酰化、选择性消除、DHP保护、水解、缩合、格氏、wittig和脱保护9步反应合成岩藻甾醇的合成路线,总收率为53.31%。该方法原料廉价易得,操作简洁高效,对环境友好,为未来岩藻甾醇的工业化生产提供一种新的思路。目标化合物的结构经^(1)H NMR、^(13)C NMR和HR-MS确证。Fucosterol(1),as a plant sterol with various medicinal activities,has broad application prospects.However,there are few natural sources of Fucosterol and the extraction rate is low.In this article,Fucosterol was synthesized from hyodeoxycholic acid(2)by methyl esterification,sulfonylation,selective elimination,DHP protection,hydrolysis,condensation,Grignard reaction,wittig reaction and deprotection in a total yield of 53.31%.The synthetic method contains several advantages,such as low-cost materials,simple and efficient operation,and environmentally friendly.In addition,it also provide a new approach for the industrial production of fucosterol in the future.The structure of the target compound was confirmed by^(1)H NMR,^(13)C NMR and HR-MS,which was consistent with the natural structure of fucosterol.

关 键 词：岩藻甾醇 猪去氧胆酸 Weinreb酰胺 格氏反应 WITTIG反应 

分 类 号：O621.3[理学—有机化学]