TAX-109, 109881, XRP-9881, RPR-109881A
Larotaxel水合物 莱龙泰素 Chemical Name: (2aR,3aR,4aR,6R,9S,11S,12S,12aR,12bS)-6,12b-Diacetoxy-9-[3(S)-(tert-butoxycarbonylamino)-2(R)-hydroxy-3-phenylpropionyloxy]-12-benzoyloxy-11-hydroxy-8,13,13-trimethyl-2a,3,3a,4,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]cyclopropa[4,5]benz[1,2-b]oxet-5-one dihydrate
CAS No. 192573-38-9, 156294-36-9 (anhydrous)
项目整合开发状态: Phase III
项目研究机构: Aventis Pharma (Originator), Bristol-Myers Squibb (Originator)
合成路线:The reaction of taxol (I) with benzyloxycarbonyl chloride and DIEA in dichloromethane gives the protected compound (II),which is treated with DAST in the same solvent to yield the cyclopropa taxol (III).The hydrogenolysis of (III) with H2 over Pd/C affords compound (IV),which is deacylated with tetrabutylammonium borohydride in dichloromethane to provide the cyclopropa baccatin (V).The acylation of (V) with azetidinone (VI) by means of BuLi in THF gives the silylated taxoid (VII),which is finally desilylated with HCl in acetonitrile to afford the target compound.
📌 参考资料/链接：
参考文献标题:7,8-Cyclopropataxones
文献作者:Chen,S.-H.; Farina,V.(Bristol-Myers Squibb Co.)
参考来源:CA 2099211; EP 0577083; JP 1994179665; JP 1994179666; JP 2001199974; US 5254580
📄 详细内容
合成路线:The reaction of the taxane derivative (I) with trifluoromethanesulfonic anhydride gives the monotriflate (II),which is treated with sodium azide in hot acetonitrile to yield the cyclopropa derivative (III).The cleavage of the oxazolidine ring of (III) by means of formic acid affords the 3-amino-2-hydroxy derivative (IV),which is finally acylated with tert-butoxycarbonyl anhydride to provide the target taxoid derivative.
参考文献标题:Novel taxoids,preparation thereof and pharmaceutical compsns.containing same
文献作者:Bouchard,H.; Buourzat,J.-D.; Commer鏾n,A.(Aventis Pharma SA)
参考来源:EP 0673372; FR 2698871; JP 1996504425; JP 1998291930; US 5814658; WO 9413654
合成路线:The reaction of the taxane derivative (I) with trifluoromethanesulfonic anhydride gives the monotriflate (II),which is treated with sodium azide in hot acetonitrile to yield the cyclopropa derivative (III).The cleavage of the oxazolidine ring of (III) by means of formic acid affords the 3-amino-2-hydroxy derivative (IV),which is finally acylated with tert-butoxycarbonyl anhydride to provide the target taxoid derivative.
参考文献标题:Method for treating abnormal cell proliferation in the brain
文献作者:Renard,A.; Bissery,M.-C.(Aventis Pharma SA)
参考来源:US 6156789
合成路线:The reaction of the taxoid compound (I) with DAST gives the cyclopropataxoid compound (II),which is finally deprotected with Zn and HOAc to yield the target compound.
参考文献标题:7-Halo and 7beta,8beta-methano-taxols,antineoplastic use and pharmaceutical compsns.containing them
文献作者:Skulnick,H.I.; Johnson,R.A.; Midy,E.G.; Kelly,R.C.; Hester,J.B.Jr.(Pharmacia Corp.)
参考来源:EP 0674630; WO 9413655
产品链接: CAS No. 192573-38-9›› 产品链接: CAS No.156294-36-9››