21-Aminoepothilone B, BMS-310705
21-氨基埃坡霉素 BChemical Name: [1S,3S(E),7S,10R,11S,12S,16R]-3-[2-[2-(Aminomethyl)thiazol-4-yl]-1-methylvinyl]-7,11-dihydroxy-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione; (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-(aminomethyl)thiazol-4-yl]vinyl]-1-oxacyclohexadecane-2,6-dione
CAS No. 280578-49-6
项目整合开发状态: Phase I
项目研究机构: Bristol-Myers Squibb (Originator), GBF (Originator)
合成路线:The reaction of epothilone B (I) with MCPBA in dichloromethane gives the N-oxide (II),which is treated with trifluoroacetic anhydride and 2,6-lutidine in dichloromethane at 70 C in a sealed tube to yield the hydroxymethyl derivative (epothilone F) (III).The reaction of (III) with diphenylphosphoryl azide (DPA) and DBU in THF affords the azidomethyl compound (IV),which is reduced with PMe3 in THF or with H2 and Lindlar catalyst in ethanol to provide the target amino epothilone.Alternatively,the hydroxymethyl derivative (epothilone F) (III) can be obtained by biochemical hydroxylation of epothilone B (I) with Actinomyces sp.strain PTA-XXX.
📌 参考资料/链接：
参考文献标题:C-21 modified epothilones
文献作者:Kim,S.-H.; Glaser,N.; Leibold,T.; Hoefle,G.; Vite,G.(Bristol-Myers Squibb Co.; Gesellschaft f黵 Biotechnologische Forschung mbH)
参考来源:DE 19907588; EP 1157023; US 6262094; WO 0050423
📄 详细内容
合成路线:The reaction of epothilone B (I) with MCPBA in dichloromethane gives the N-oxide (II),which is treated with trifluoroacetic anhydride and 2,6-lutidine in dichloromethane at 70 C in a sealed tube to yield the hydroxymethyl derivative (epothilone F) (III).The reaction of (III) with diphenylphosphoryl azide (DPA) and DBU in THF affords the azidomethyl compound (IV),which is reduced with PMe3 in THF or with H2 and Lindlar catalyst in ethanol to provide the target amino epothilone.Alternatively,the hydroxymethyl derivative (epothilone F) (III) can be obtained by biochemical hydroxylation of epothilone B (I) with Actinomyces sp.strain PTA-XXX.
参考文献标题:Synergistic methods and compsns.for treating cancer
文献作者:Lee,F.Y.(Bristol-Myers Squibb Co.)
参考来源:WO 0172721
合成路线:The reaction of epothilone B (I) with MCPBA in dichloromethane gives the N-oxide (II),which is treated with trifluoroacetic anhydride and 2,6-lutidine in dichloromethane at 70 C in a sealed tube to yield the hydroxymethyl derivative (epothilone F) (III).The reaction of (III) with diphenylphosphoryl azide (DPA) and DBU in THF affords the azidomethyl compound (IV),which is reduced with PMe3 in THF or with H2 and Lindlar catalyst in ethanol to provide the target amino epothilone.Alternatively,the hydroxymethyl derivative (epothilone F) (III) can be obtained by biochemical hydroxylation of epothilone B (I) with Actinomyces sp.strain PTA-XXX.
参考文献标题:Microbial transformation method for the preparation of an epothilone
文献作者:Matson,J.A.; Lam,K.S.; Huang,X.; Li,W.; McClure,G.A.(Bristol-Myers Squibb Co.)
参考来源:WO 0039276
产品链接: CAS No. 280578-49-6››