【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。更多还原

【Abstract】 The improved synthesis route of( 25 R)-26-hydroxycholesterol was accomplished in 54% overall yield with the mild conditions and simple operation. The final compound( 25 R)-Cholest-5-ene-3β,26-diol was synthesized from diosgenin as the starting material in five steps. Ring opening reactioin of diosgenin gave the( 25 R)-Cholest-5-en-3β,16β,26-triol.( 25 R)-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( 25 R)-26-hydroxycholesterol. The structures of the key intermediate and target compound were confirmed by1 H NMR and HRMS.更多还原