Fluasterone, HE-2500, 8354
Chemical Name: 16alpha-Fluoroandrost-5-en-17-one
CAS No. 112859-71-9
项目整合开发状态: Phase II
项目研究机构: Temple University (Originator), Aeson Therapeutics (Licensee), Hollis-Eden (Licensee)
合成路线:Beckmann rearrangement of oxime (I) in the presence of p-acetamidobenzenesulfonyl chloride and pyridine afforded acetamide (II).Subsequent fluorination of (II) using perchloryl fluoride produced fluoroenamide (III),which was hydrolyzed with HCl to give fluoroketone (IV).After treatmentof (IV) with o-phenylenephosphorochloridite (V) and pyridine,the intermediate phosphite ester (VI) was converted to iodide (VII) by means of iodine in CH2Cl2.Finally,reductive deiodination of (VI) with Zn in AcOH produced the target compound.
合成路线:Dehydroepiandrosterone (VIII) was treated with o-phenylenephosphorochloridite (V) and then with iodine to afford iodide (IX),which was reduced to (X) by means of Zn and AcOH.Bromination of (X) with CuBr2 gave bromoketone (XI),and this was hydrolyzed to hydroxyketone (XII) upon treatment with aqueous NaOH in the presence of pyridine and oxygen.Subsequent treatment of (XII) with diethyl (2-chloro-1,1,2-trifluoroethyl)amine (XIII) afforded the target fluoroketone
📌 参考资料/链接：
参考文献标题:Steroids useful as anti-cancer and anti-obesity agents,a therapeutic compsn.containing them and use thereof for the preparation of a therapeutic compsn.
文献作者:Lewbart,M.L.; Schwartz,A.G.(Research Corporation Technologies,Inc.)
参考来源:EP 0246650; JP 1987283993
📄 详细内容
合成路线:Beckmann rearrangement of oxime (I) in the presence of p-acetamidobenzenesulfonyl chloride and pyridine afforded acetamide (II).Subsequent fluorination of (II) using perchloryl fluoride produced fluoroenamide (III),which was hydrolyzed with HCl to give fluoroketone (IV).After treatmentof (IV) with o-phenylenephosphorochloridite (V) and pyridine,the intermediate phosphite ester (VI) was converted to iodide (VII) by means of iodine in CH2Cl2.Finally,reductive deiodination of (VI) with Zn in AcOH produced the target compound.
合成路线:Dehydroepiandrosterone (VIII) was first brominated with CuBr2 to give bromoketone (XIV),which was hydrolyzed to hydroxyketone (XV).After protection of (XV) as the monoacetate (XVI),fluorination at position 16 by means of (2-chloro-1,1,2-trifluoroethyl)amine (XIII) afforded fluoroketone (XVII).Ester hydrolysis in (XVI) then gave intermediate (IV).
参考文献标题:17-Hydroxy-steroids
文献作者:Schwartz,A.G.; Lewbart,M.L.
参考来源:US 4898694
产品链接: CAS No. 112859-71-9››