网站主页>>>项目整合精选>>>项目整合精选>>>Dienogest, MJR-35, M-18575, STS-557, Climodien(comb. with estradiol valerate), Klimodien(comb. with estradiol valerate), Valette(comb. with ethinyl estradiol), Endometrion

Dienogest, MJR-35, M-18575, STS-557, Climodien(comb. with estradiol valerate), Klimodien(comb. with estradiol valerate), Valette(comb. with ethinyl estradiol), Endometrion

地诺孕素Chemical Name: 17alpha-Cyanomethyl-17beta-hydroxy-13beta-methylgona-4,9-dien-3-one; (17alpha)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile
CAS No. 65928-58-7
项目整合开发状态: Launched-1990
项目研究机构: Jenapharm (Originator), Schering AG (Originator), Innothera (Licensee), Mochida (Licensee)
合成路线:The bromination of 17-alpha-cyanomethyl-17-beta-hydroxy-13-beta-methylgona-5(10)-ene-3-one (I) with polyvinylpyridinium bromide perbromide yields dibromide (II),which immediately debrominates to the final product.
📌 参考资料/链接:
参考文献标题:Verfahren zur herstellung von steroiden mit einem 4,9-diensystem
文献作者:Huebner,M.; Menzenbach,B.(Akademie der Wissenschaften der DDR)
参考来源:DD 205170

📄 详细内容


合成路线:1,4-Dihydroestronemethylether (I) was reacted with dimethylsulfonium-methylide (A) in a highly stereoselective manner to give the oxirane (II),which formed the cyanomethyl compound (III) by the addition of sodium cyanide.(III) was hydrolyzed with oxalic acid (B) in methanol and the product (IV) treated with pyridine perbromide hydrobromide to the dibromoketone,which yielded STS-557 after dehydrobromination.

参考文献标题:STS-557
文献作者:Unterhalt,B.
参考来源:Drugs Fut 1980,5(6),311


合成路线:1,4-Dihydroestronemethylether (I) was reacted with dimethylsulfonium-methylide (A) in a highly stereoselective manner to give the oxirane (II),which formed the cyanomethyl compound (III) by the addition of sodium cyanide.(III) was hydrolyzed with oxalic acid (B) in methanol and the product (IV) treated with pyridine perbromide hydrobromide to the dibromoketone,which yielded STS-557 after dehydrobromination.

参考文献标题:Synthesis and reactions of oxiranes obtained from 3- and 17-keto steroids
文献作者:Cook,C.E.; et al.
参考来源:J Org Chem 1968,332789


合成路线:1,4-Dihydroestronemethylether (I) was reacted with dimethylsulfonium-methylide (A) in a highly stereoselective manner to give the oxirane (II),which formed the cyanomethyl compound (III) by the addition of sodium cyanide.(III) was hydrolyzed with oxalic acid (B) in methanol and the product (IV) treated with pyridine perbromide hydrobromide to the dibromoketone,which yielded STS-557 after dehydrobromination.

参考文献标题:Ein vereinfachtes Verfahren zur Darstellung von Steroid-Spirooxiranen
文献作者:H黚ner,M.; et al.
参考来源:J Prakt Chem 1972,314667


合成路线:1,4-Dihydroestronemethylether (I) was reacted with dimethylsulfonium-methylide (A) in a highly stereoselective manner to give the oxirane (II),which formed the cyanomethyl compound (III) by the addition of sodium cyanide.(III) was hydrolyzed with oxalic acid (B) in methanol and the product (IV) treated with pyridine perbromide hydrobromide to the dibromoketone,which yielded STS-557 after dehydrobromination.

参考文献标题:Prostagene vom Typ 17alpha-CH2X-substituierter 19-Nortestossteronderivate
文献作者:Ponsold,K.; et al.
参考来源:Pharmazie 1978,33792


合成路线:1,4-Dihydroestronemethylether (I) was reacted with dimethylsulfonium-methylide (A) in a highly stereoselective manner to give the oxirane (II),which formed the cyanomethyl compound (III) by the addition of sodium cyanide.(III) was hydrolyzed with oxalic acid (B) in methanol and the product (IV) treated with pyridine perbromide hydrobromide to the dibromoketone,which yielded STS-557 after dehydrobromination.
参考文献标题:A new class of active steroids: the 19-nor-delta(4,9)-3-ketosteroids
文献作者:Perelman,M.; et al.
参考来源:J Am Chem Soc 1960,822402


产品链接: CAS No. 65928-58-7››