TAX-258, XRP-6258, RPR-116258A, TXD-258

卡巴他赛Chemical Name: [2aR[2aalpha,4beta,4abeta,6beta,9alpha(2R,3S),11beta,12alpha,12aalpha,12balpha]]-12b-Acetoxy-9-[3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionyloxy]-12-(benzoyloxy)-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-5-one; 3'-(tert-Butoxycarbonylamino)-10-O-deacetyl-3'-debenzamido-7,10-O-dimethylpaclitaxel
CAS No. 183133-96-2
项目整合开发状态: Phase II
项目研究机构: Aventis Pharma (Originator)
合成路线:Protection of 10-deacetylbaccatin III (I) with chlorotriethylsilane in pyridine affords the 7,13-bis-silyl ether (II),which upon alkylation by means of iodomethane and NaH provides the 10-methoxy derivative (III).After desilylation of (III) by means of a hydrogen fluoride-triethylamine complex,the deprotected triol (IV) is methylated with iodomethane and NaH to yield the 7,10-dimethyl ether (V).Esterification of (V) with the oxazolidinecarboxylic acid (VI) in the presence of DCC/DMAP furnishes (VII).(1,2)

合成路线:Selective hydrolysis of the oxazolidine moiety of (VII) under smooth acidic conditions gives yields the hydroxy amino ester derivative.(1,2)