Tipredane, SQ-27239
替泼尼旦Chemical Name: 17alpha-(Ethylsulfanyl)-9alpha-fluoro-11beta-hydroxy-17beta-(methylsulfanyl)androsta-1,4-dien-3-one
CAS No. 85197-77-9
项目整合开发状态: Phase III
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:Oxidation of commercially available 9-fluoroprednisolone (I) with sodium bismuthate gives the ketone (II),which is reacted with methanethiol in a mixture of dichloromethane and acetic acid in the presence of boron trifluoride etherate to give the thioketal (III).Acetylation of (III) with acetic anhydride in pyridine containing 4-dimethylaminopyridine gives the acetate (IV),which is heated in diethylbenzene to give the vinyl sulfide (V).The addition of ethanethiol to (V) at low temperatures in the presence of boron trifluoride etherate or trifluoroacetic acid in dichloromethane proceeds with high stereoselectivity to give the thioketal (VI),which is deacetylated with sodium hydroxide in methanol to give tipredane.
📌 参考资料/链接：
参考文献标题:Antiinflammatory 17,17-bis(substd.thio)androstene
文献作者:Varma,R.K.(Bristol-Myers Squibb Co.)
参考来源:US 4361559
📄 详细内容
合成路线:Oxidation of commercially available 9-fluoroprednisolone (I) with sodium bismuthate gives the ketone (II),which is reacted with methanethiol in a mixture of dichloromethane and acetic acid in the presence of boron trifluoride etherate to give the thioketal (III).Acetylation of (III) with acetic anhydride in pyridine containing 4-dimethylaminopyridine gives the acetate (IV),which is heated in diethylbenzene to give the vinyl sulfide (V).The addition of ethanethiol to (V) at low temperatures in the presence of boron trifluoride etherate or trifluoroacetic acid in dichloromethane proceeds with high stereoselectivity to give the thioketal (VI),which is deacetylated with sodium hydroxide in methanol to give tipredane.
参考文献标题:Tipredane
文献作者:Varma,R.K.
参考来源:Drugs Fut 1988,13(8),739
产品链接: CAS No. 85197-77-9››