专利号:US-8293930-B1 优先权日:2004-06-25 标题 :One pot synthesis of taxane derivatives and their conversion to paclitaxel and docetaxel 发明人:NAIDU RAGINA 权利人:NAIDU RAGINA; CHATHAM BIOTEC LTD 摘要:A process is provided for the semi-synthesis of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis of protected taxane intermediate in a one pot reaction of protecting the C-7 and C-10 positions and attaching a side chain at the C-13 position and subsequently deprotecting the group to form paclitaxel or docetaxel, and taxane intermediates.
专利号:US-7893283-B2 优先权日:2004-06-04 标题:Semi-synthesis of taxane intermediates and their conversion to paclitaxel and docetaxel 发明人:NAIDU RAGINA 权利人:CHATHAM BIOTEC LTD 摘要:A process is provided for the semi-synthesis of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis of protected taxane intermediates.
专利号:US-6576777-B2 优先权日:1996-10-18 标 题:Semi-synthesis of a protected baccatin III compound 发明人:ZAMIR LOLITA; CARON GAETAN 权利人:INST NAT RECH SCIENT 摘要:The present invention relates to a semi-synthetic process to convert a naturally occurring taxane into a suitable starting material for the synthesis of paclitaxel and related compounds. Specifically, the present invention relates to a process for the conversion of 9-dihydro-13-acetylbaccatin III into a 7-protected baccatin III which can then be used as starting material for the synthesis of taxane derivatives such as paclitaxel, docetaxel, cephalomannine and other taxanes structurally related to baccatin III. The method as described uses a preparative scale technique which is amenable to commercial scale-up.
专利号:WO-2008032104-A1 优先权日:2006-09-15 标题:One pot synthesis of taxane derivatives and their conversion to paclitaxel and docetaxel 发明人:WALKER ROSS THOMSON; NAIDU RAGINA 权利人:CHATHAM BIOTEC LTD; WALKER ROSS THOMSON; NAIDU RAGINA 摘要:A process is provided for the semi-synthesis of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis of protected taxane intermediate in a one pot reaction, of protecting the C-10 and attaching a side chain at C-13 position and subsequently deprotecting the group to form paclitaxel or docetaxel, and intermediates used therein.
专利号:WO-0134589-A1 优先权日:1999-11-05 标 题 :Semi-synthesis of baccatin iii from 9-dihydro-13-acetylbaccatin iii 发明人:ZAMIR LOLITA 权利人:ZAMIR LOLITA 摘要:The present invention relates to a semi-synthetic process to convert a naturally occurring taxane into a suitable starting material for the synthesis of paclitaxel and related compounds. Specifically, the present invention relates to a process for the conversion of 9-dihydro-13-acetylbaccatin III into baccatin III which can then be used as starting material for the synthesis of taxane derivatives such as paclitaxel, docetaxel, cephalomannine and other taxanes structurally related to baccatin III.
专利号:US-7202370-B2 优先权日:2003-10-27 标 题 :Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III 发明人:NAIDU RAGINA 权利人:CONOR MEDSYSTEMS INC 摘要:A method is provided for the semi-synthesis of taxane intermediates useful in the preparation of paclitaxel and docetaxel from 9-dihydro-13-acetylbaccatin III. The preparation of a suitably protected baccatin III backbone from 9-dihydro-13-acetylbaccatin III, and the insertion of the phenylisoserine side chain onto the protected baccatin III from 9-dihydro-13-acetylbaccatin III to form the taxane derivatives, paclitaxel and docetaxel is disclosed.
1: Grobosch T, Schwarze B, Stoecklein D, Binscheck T. Fatal poisoning with Taxus baccata: quantification of paclitaxel (taxol A), 10-deacetyltaxol, baccatin III, 10-deacetylbaccatin III, cephalomannine (taxol B), and 3,5-dimethoxyphenol in body fluids by liquid chromatography-tandem mass spectrometry. J Anal Toxicol. 2012 Jan-Feb;36(1):36-43. doi: 10.1093/jat/bkr012. doi: 10.1042/CBR20110001. Epub 2011 Apr 8. 3: Fu Y, Zu Y, Li S, Sun R, Efferth T, Liu W, Jiang S, Luo H, Wang Y. Separation of 7-xylosyl-10-deacetyl paclitaxel and 10-deacetylbaccatin III from the remainder extracts free of paclitaxel using macroporous resins. J Chromatogr A. 2008 Jan 4;1177(1):77-86. Epub 2007 Nov 17. Epub 2007 Aug 9. Epub 2006 Nov 9. Epub 2006 Sep 8. Epub 2006 Aug 4.
合成参考文献
参考文献:10.1021/np960647q 摘要:Zhang J, Zhang L, Wang X, Qiu D, Sun D, Gu J, Fang Q. Microbial Transformation of 10-Deacetyl-7-epitaxol and 1β-Hydroxybaccatin I by Fungi from the Inner Bark of Taxus yunnanensis. J. Nat. Prod. 1998 Mar 21;61(4):497–500. doi: 10.1021/np960647q.