摘要
本研究对(25R)-26-羟基胆固醇的合成路线及方法进行了改进。以薯蓣皂苷元为起始物,经开环反应得到(25R)-3-羟基基胆甾-5-烯-16,26-二醇,再经叔丁基二甲基氯硅烷保护C3-和C26-位羟基后依次经磺酰化、四氢铝锂还原得到(25R)-3,26-二叔丁基二甲硅氧基-5-烯,最后经四丁基氟化铵脱保护得到(25R)-26-羟基胆固醇,总收率54%。改进后路线具有条件温和,分离纯化简便等优点。所合成关键中间体及目标化合物经核磁氢谱、高分辨质谱确证。
The improved synthesis route of(25R)-26-hydroxycholesterol was accomplished in 54%overall yield with the mild conditions and simple operation.The final compound(25R)-Cholest-5-ene-3β,26-diol was synthesized from diosgenin as the starting material in five steps.Ring opening reactioin of diosgenin gave the(25R)-Cholest-5-en-3β,16β,26-triol.(25R)-3β,26-Bis[(tert-butyldimethylsilyl)oxy]-cholest-5-ene was obtained by hydroxyl protection with tert-butyldimethylsilyl,sulfonylation and reduction with lithium aluminum hydride,respectively.The later was subjected to deprotection with tetrabutylammonium fluoride to afford the(25R)-26-hydroxycholesterol.The structures of the key intermediate and target compound were confirmed by 1H NMR and HRMS.
作者
曾倩倩
徐嘉琪
陈峰
杨学军
赵志刚
杨鸿均
Zeng Qianqian;Xu Jiaqi;Chen Feng;Yang Xuejun;Zhao Zhigang;Yang Hongjun(School of Chemistry and Environmental Protection Engineering,Southwest Minzu University,Chengdu 610041,China)
出处
《山东化工》
CAS
2018年第3期26-27,30,共3页
Shandong Chemical Industry
基金
西南民族大学研究生创新型科研项目(CX2017SZ015)
