新产品编号:968693

Chemical Name: (15alpha,17beta)-3,17-Dihydroxyestra-1,3,5(10)-triene-15-carboxylic acid ethyl ester
CAS No. 534572-73-1
项目整合开发状态: Preclinical
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:The known phenolic steroid derivative (I) is protected as the corresponding benzyl ether (II) with benzyl bromide in the presence of K2CO3 and i-Pr2NEt.Subsequent ketal hydrolysis in (II) under acidic conditions furnishes the unsaturated ketone (III).Conjugate addition of NaCN to (III) in aqueous THF at reflux gives the 15-beta-cyano steroid (IV).The keto group of (IV) is then reduced with NaBH4 to yield alcohol (V).Hydrolysis of the nitrile group of (V) with KOH in ethyleneglycol leads to the epimerized 15-alpha-carboxylic acid (VI).The O-benzyl protecting group of (VI) is then removed by catalytic hydrogenolysis to provide phenol (VII).Finally,Fischer esterification of acid (VII) with EtOH and sulfuric acid leads to the title ethyl ester.