紫杉醇置于双氧水,碳酸氢钠体系中,用 四氢呋喃 作为反应溶剂,化学反应 24.0H,以95%的收率获得产物7-表-10-脱乙酰基紫杉醇 参考文献:Deacetylation Of Paclitaxel And Other Taxanes 标题:Deacetylation Of Paclitaxel And Other Taxanes 摘要:10-Deacetyltaxol Is Prepared From Paclitaxel In 956 Yield By Using H2O2 In The Presence Of Nahco3. DOI:10.1016/0040-4039(95)00212-U
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: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:US-6458568-B1 优先权日:1998-05-22 标题 :Method for the production of baccatin-III by enzymatic synthesis 发明人:GLUND KONRAD; HOFFMANN MATTHIAS; WECKWERTH WOLFRAM; ZOCHER RAINER 权利人:INST BIOANALYTIK UMWELT TOXIKO 摘要:A method for the continuous synthesis of baccatin-III is performed by means of the enzymatic acetylations of 10-deacetyl baccatin-III (10-DAB) in an enzyme reactor. This objective is accomplished by a method, for which an aqueous reaction batch is used, which contains a partially purified or a very pure acetyl transferase from a Taxus species and synthesis components, especially 10-DAB, acetyl compounds or optionally an acetyl coenzyme A, which can be regenerated, a protective colloid and optionally a buffer substance in solution. The solution is separated by a semipermeable membrane from an organic solvent, which serves as extraction agent for baccatin-III, the reaction batch being regenerated at regular intervals in an aqueous buffer system and the solvent continuously being exchanged. By conducting the reaction, the product can be removed continuously from the reaction batch for the partial synthesis of taxol and taxoter. By the above method, achievable yields are increased significantly.
专利号:US-7838694-B2 优先权日:2004-04-23 标题 :Semi-synthesis and isolation of taxane intermediates from a mixture of taxanes 发明人:NAIDU RAGINA; FOO SAMUEL SIANG KIANG 权利人:CHATHAM BIOTEC LTD 摘要:A process is provided for the semi-synthesis and isolation of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis and isolation of 10-deacetylbaccatin III, the semi-synthesis of a mixture of 10-deacetylbaccatin III and baccatin III, and protected derivatives thereof, from a mixture of taxanes.
专利号:US-7906661-B2 优先权日:2004-06-29 标 题 :Semi-synthetic conversion of paclitaxel to docetaxel 发明人:NAIDU RAGINA; FOO SAMUEL SIANG KIANG; XUE BAOYU; FAN BO 权利人:CHATHAM BIOTEC LTD 摘要:A process is provided for the semi-synthesis of taxane derivatives useful in the preparation of docetaxel, in particular, the semi-synthesis of protected taxane derivatives in a one pot reaction of protecting the C-2′, C-7 and C-10 positions and introducing a t-Boc group at the nitrogen of the amide group at the C-3′ position in paclitaxel and subsequently conversion to docetaxel, and derivatives used therein.
1: Li BJ, Wang H, Gong T, Chen JJ, Chen TJ, Yang JL, Zhu P. Improving 10-deacetylbaccatin III-10-β-O-acetyltransferase catalytic fitness for Taxol production. Nat Commun. 2017 May 18;8:15544. doi: 10.1038/ncomms15544. Erratum in: Nat Commun. 2018 Jul 13;9:16221. doi: 10.1038/ncomms16221. 2: Helson L. Cephalomannine and 10-deacetyltaxol cytotoxicity in human glial and neuroblastoma cell-lines. Int J Oncol. 1993 Feb;2(2):297-9. 44(3):312-9. doi: 10.1021/np50015a013.
合成参考文献
参考文献:10.1038/ki.1997.222 摘要:Woo DD, Tabancay AP, Wang CJ. Microtubule active taxanes inhibit polycystic kidney disease progression in cpk mice. Kidney Int. 1997 May;51(5):1613–8. doi: 10.1038/ki.1997.222. 参考文献:10.1081/jlc-100102056 摘要:Park YK, Chung ST, Row KH. PREPARATIVE CHROMATOGRAPHIC SEPARATION OF TAXOL FROM YEW TREES. Journal of Liquid Chromatography & Related Technologies. 1999 Jan;22(18):2755–61. doi: 10.1081/jlc-100102056. 参考文献:10.1016/s0021-9673(97)01174-6 摘要:Theodoridis G, Laskaris G, de Jong CF, Hofte AJP, Verpoorte R. Determination of paclitaxel and related diterpenoids in plant extracts by high-performance liquid chromatography with UV detection in high-performance liquid chromatography–mass spectrometry. Journal of Chromatography A. 1998 Apr;802(2):297–305. doi: 10.1016/s0021-9673(97)01174-6. 参考文献:10.1016/j.bmcl.2007.04.058 摘要:Ballatore C, Hyde E, Deiches RF, Lee VM-, Trojanowski JQ, Huryn D, Smith AB. Paclitaxel C-10 carbamates: Potential candidates for the treatment of neurodegenerative tauopathies. Bioorganic & Medicinal Chemistry Letters. 2007 Jul;17(13):3642–6. doi: 10.1016/j.bmcl.2007.04.058. 参考文献:10.1038/s42003-019-0744-4 摘要:Yang L, Chen T, Wang F, Li L, Yu W, Si Y, Chen J, Liu W, Zhu P, Gong W. Structures of β-glycosidase LXYL-P1-2 reveals the product binding state of GH3 family and a specific pocket for Taxol recognition. Communications Biology. 2020 Jan 10;3(1):22. doi: 10.1038/s42003-019-0744-4.