虫草素的合成工艺研究

Study on the synthetic process of corgycepin

目的优化虫草素的合成工艺条件及路线。方法以腺苷为起始原料,与2-乙酰氧基异丁酰溴反应得到5′-O-(2,5,5-三甲基-1,3-二氧戊环-4-氧亚基-2-基)-3′-溴-3′-去羟基-2′-O-乙酰腺苷(4)及其异构体5′-O-(2,5,5-三甲基-1,3-二氧戊环-4-氧亚基-2-基)-2′-溴-2′-去羟基-3′-O-乙酰腺苷的混合物,经纯化去除2′位的溴取代异构体后得到关键中间体4,4经酸水解、催化氢解反应得到虫草素。结果与结论目标化合物虫草素及中间体的结构经^(1)H-NMR、^(13)C-NMR和ESI-MS谱确证,目标化合物总收率为31.7%,纯度为99.8%(HPLC法)。本工艺优化了虫草素的合成反应条件和后处理方法,提高了中间体及目标化合物的收率,操作简单,适合大规模工业化生产。

An improved synthetic process of cordycepin was reported.The key intermediate 5′-O-(2,5,5-trimethyl-1,3-dioxolan-4-oxo-2-yl)-3′-bromo-3′-deoxy-2′-O-acetyl adenosine was synthesized from adenosine and 2-acetoxy-isobutyryl bromide,and isolated from the isomers.Then the target compound corgycepin was obtained by acidic hydrolysis and hydrogenolysis reaction.The chemical structures of corgycepin and some key intermediates were identified by^(1)H-NMR,^(13)C-NMR and ESI-MS.The total yield was 31.7%and the purity of the target compound was 99.8%(HPLC).The improved process has several advantages such as simple operation,high yield and purity,which is suitable for large scale preparation.