Paclitaxel ceribate, Protaxel, BP-179
Chemical Name: 3(S)-Benzamido-2(R)-hydroxybenzenepropionic acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-diacetoxy-12-(benzoyloxy)-4-[(2,3-dihydroxypropoxy)carbonyloxy]-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-9-yl ester; 4-[(2,3-Dihydroxypropoxy)carbonyloxy]taxol; [2aR-[2aalpha,4beta,4abeta,6beta,9alpha(2R*,3S*),11beta,12alpha,12aalpha,12balpha]]-6,12b-Diacetoxy-9-(3-benzamido-2-hydroxy-3-phenylpropoxy)-12-benzoyloxy-4-(2,3-dihydroxypropoxycarbonyloxy)-11-hydroxy-4a,8,13,13-tetramethyl-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclododeca[3,4]benz[1,2-b]oxet-5-one
CAS No. 186040-50-6
项目整合开发状态: Phase I/II
项目研究机构: Interpharma Praha (Orphan Drug), Biophysica Foundation (Originator), Interpharma Praha (Codevelopment)
合成路线:Acylation of paclitaxel (I) with 2,3-O-isopropylideneglyceryl chloroformate (II) produced the 2',7-bis-carbonate (III).Subsequent acid hydrolysis of the acetonide groups of (III) furnished the corresponding bis-(dihydroxypropyl)carbonate (IV).The 2'-ester of (IV) was then selectively hydrolyzed using a phosphate buffer at pH 6.5.
📌 参考资料/链接：
参考文献标题:Novel taxoids
文献作者:Sovak,M.; Douglass,J.G.; Bressi,J.C.; Seligson,A.(Biophysica Foundation)
参考来源:JP 1998509461; US 5801191; WO 9638138
📄 详细内容
合成路线:Acylation of paclitaxel (I) with 2,3-O-isopropylideneglyceryl chloroformate (II) produced the 2',7-bis-carbonate (III).Subsequent acid hydrolysis of the acetonide groups of (III) furnished the corresponding bis-(dihydroxypropyl)carbonate (IV).The 2'-ester of (IV) was then selectively hydrolyzed using a phosphate buffer at pH 6.5.
合成路线:In an alternative method,paclitaxel (I) was acylated with allyl chloroformate (V) to afford the bis-carbonate (VI).Dihydroxylation of both allyl groups of (VI) was accomplished by treatment with tert-butyl hydroperoxide producing (IV).The 2'-ester of (IV) was finally removed upon stirring in a NaHCO3-neutralized solution at room temperature.
参考文献标题:A new prodrug of paclitaxel: Synthesis of Protaxel
文献作者:Seligson,A.L.; Terry,R.C.; Bressi,J.C.; Douglass,J.G.III; Sovak,M.
参考来源:Anti-Cancer Drugs 2001,12(4),305
产品链接: CAS No. 186040-50-6››