新产品编号:644383
Chemical Name: (1S,3S,7S,10R,11S,12S,16S)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[1-methyl-2(E)-(2-methylthiazol-4-yl)vinyl]-4-oxabicyclo[14.1.0]heptadecane-5,9-dione
CAS No. 247230-49-5
项目整合开发状态: Biological Testing
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:Deoxygenation of epothilone B (I) by means of tungsten hexachloride and butyllithium produced the olefin epothilone D (II).After protection of (II) as the bis-O-silylated derivative (III),cyclopropanation with chloroiodomethane and diethylzinc afforded the cyclopropane adduct (IV).A higher yield procedure to prepare (IV) involved addition of dibromocarbene,generated from bromoform and NaOH under phase-transfer conditions,to olefin (II),followed by reduction of the resulting dibromocyclopropane (V) with azobisisobutyronitrile.Finally,desilylation employing trifluoroacetic acid furnished the title compound.
📌 参考资料/链接：
参考文献标题:12,13-Modified epothilone derivs.
文献作者:Kim,S.-H.K.; Vite,G.D.; Hofle,G.(Bristol-Myers Squibb Co.)
参考来源:WO 9954318; WO 9954319
📄 详细内容
合成路线:Deoxygenation of epothilone B (I) by means of tungsten hexachloride and butyllithium produced the olefin epothilone D (II).After protection of (II) as the bis-O-silylated derivative (III),cyclopropanation with chloroiodomethane and diethylzinc afforded the cyclopropane adduct (IV).A higher yield procedure to prepare (IV) involved addition of dibromocarbene,generated from bromoform and NaOH under phase-transfer conditions,to olefin (II),followed by reduction of the resulting dibromocyclopropane (V) with azobisisobutyronitrile.Finally,desilylation employing trifluoroacetic acid furnished the title compound.
参考文献标题:288555
文献作者:Johnson,J.; Kim,S.H.; Bifano,M.; DiMarco,J.; Fairchild,C.; Gougoutas,J.; Lee,F.; Long,B.; Tokarski,J.; Vite,G.
参考来源:Drug Data Rep 2000,22(8),686