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目的改进多烯紫杉醇的合成工艺,寻找一条适合于工业生产的切实可行的合成路线。方法以顺式肉桂酸乙酯为起始原料,经不对称环氧化、叠氮开环、氢化等反应制备唑烷羧酸型侧链;将该侧链与选择性保护的母核结构—10-去乙酰基巴卡亭Ⅲ连接,经酯化、脱保护基反应合成多烯紫杉醇。结果目标化合物的结构经1H-NMR、13C-NMR、MS、IR、元素分析确证,合成C13位手性侧链的收率为66%,酯化及脱保护反应的收率为60%。结论新工艺路线采用低成本原料,简单可行,适合于工业化生产。
Objective To improve the synthesis of docetaxel and to find a viable synthetic route suitable for industrial production. Methods The cis-ethyl cinnamate was used as the starting material to prepare the oxazolidine-type side-chain by asymmetric epoxidation, azide ring-opening and hydrogenation. The side chain and the selectively protected core structure -10-deacetyl baccatin Ⅲ connection, the esterification, deprotection reaction synthesis docetaxel. Results The structure of the target compound was confirmed by 1H-NMR, 13C-NMR, MS, IR and elemental analysis. The yield of the chiral side chain synthesized at C13 was 66%, and the yield of esterification and deprotection was 60%. Conclusion The new process route using low-cost raw materials, simple and feasible, suitable for industrial production.