Oxidation of glycoside substituted taxanes to taxol or taxol precursors
and new taxane compounds formed as intermediates
    23.
    发明授权
    Oxidation of glycoside substituted taxanes to taxol or taxol precursors and new taxane compounds formed as intermediates 失效
    将糖苷取代的紫杉烷氧化成紫杉醇或紫杉醇前体和形成为中间体的新的紫杉烷化合物

    公开(公告)号:US5412116A

    公开(公告)日:1995-05-02

    申请号:US133449

    申请日:1993-10-07

    摘要: A process for the conversion of glycoside substituted taxanes to taxol and related compounds that can serve as precursors to taxol. The process includes the oxidation of glycoside substituted taxanes to convert the glycoside to the hydroxyl group. The oxidation can occur in the presence of an acid or followed by treatment with acid. Application of the process to 7-xylosyl taxol ("XT") yields taxol; application to other glycoside substituted taxanes forms compounds that can serve as precursors for taxol. The process includes the formation of certain new taxol related intermediate compounds having a hemialdal at the C-7 site on the taxane ring, which hemialdal can then be converted to taxol or taxol precursors. Since glycoside substituted taxanes are isolated with taxol from naturally occurring biomass, their conversion to taxol using the process of the present invention significantly improves the total yield of taxol from natural sources.

    摘要翻译: 将糖苷取代的紫杉烷转化为紫杉醇和可用作紫杉醇前体的相关化合物的方法。 该方法包括糖苷取代的紫杉烷的氧化以将糖苷转化为羟基。 氧化可以在酸的存在下发生,或者随后用酸处理。 该方法应用于7-木糖基紫杉醇(“XT”)产生紫杉醇; 应用于其他糖苷取代的紫杉烷形成可用作紫杉醇前体的化合物。 该过程包括在紫杉烷环上的C-7位点处形成具有半透明质酸的某些新的紫杉醇相关的中间体化合物,然后可将该血液转化为紫杉醇或紫杉醇前体。 由于糖苷取代的紫杉烷与天然存在的生物质的紫杉醇分离,因此使用本发明的方法转化成紫杉醇显着地提高了紫杉醇的天然来源总产量。