Ixabepilone, 16-Aza-epothilone B, BMS 247550-01, NSC-710428, BMS-247550
伊沙匹隆Chemical Name: (4S,7R,8S,9S,13R,14S,16S)-13,14-Epoxy-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2(E)-(2-methylthiazol-4-yl)vinyl]-1-azacyclohexadecane-2,6-dione; (1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
CAS No. 219989-84-1
项目整合开发状态: Phase III
项目研究机构: Bristol-Myers Squibb (Originator), National Cancer Institute (Not Determined)
合成路线:The cleavage of the lactone group of epothilone B (I) by means of Na-N3 and tetrakis triphenylphosphine palladium (0) in THF gives the azido carboxylic acid (II),which is reduced with polymer-supported PPH3 (or in solution) or with H2 over PtO2 in ethanol to yield the amino acid (III).Finally,this compound is cyclized by means of diphenylphosphoryl azide (DPPA) in DMF.
📌 参考资料/链接：
参考文献标题:A process for the preparation of ring-opened epothilone intermediates which are useful for the preparation of epothilone analogs
文献作者:Borzilleri,R.M.; Soong-Hoon,K.(Bristol-Myers Squibb Co.)
参考来源:WO 9927890
📄 详细内容
合成路线:The cleavage of the lactone group of epothilone B (I) by means of Na-N3 and tetrakis triphenylphosphine palladium (0) in THF gives the azido carboxylic acid (II),which is reduced with polymer-supported PPH3 (or in solution) or with H2 over PtO2 in ethanol to yield the amino acid (III).Finally,this compound is cyclized by means of diphenylphosphoryl azide (DPPA) in DMF.
参考文献标题:Epothilone derivs.
文献作者:Vite,G.D.; Kim,S.-H.; Johnson,J.A.; Borzilleri,R.M.(Bristol-Myers Squibb Co.)
参考来源:WO 9902514
合成路线:The cleavage of the lactone group of epothilone B (I) by means of Na-N3 and tetrakis triphenylphosphine palladium (0) in THF gives the azido carboxylic acid (II),which is reduced with polymer-supported PPH3 (or in solution) or with H2 over PtO2 in ethanol to yield the amino acid (III).Finally,this compound is cyclized by means of diphenylphosphoryl azide (DPPA) in DMF.
参考文献标题:A novel application of a Pd(0)-catalyzed nucleophilic substitution reaction to the regio- and stereoselective synthesis of lactam analogues of the epothilone natural products
文献作者:Borzilleri,R.M.; Zheng,X.; Schmidt,R.J.; et al.
参考来源:J Am Chem Soc 2000,122(37),8890
产品链接: CAS No. 219989-84-1››