新产品编号:1633133
Chemical Name: (1S,3S)-3-[4-(Phenoxy)phenylsulfonyl]cyclohexanethiol
项目整合开发状态: Biological Testing
项目研究机构: Pfizer (Originator)
合成路线:Michael addition of 4-(phenylsulfanyl)thiophenol (II) to cyclohexenone (I) afforded the ketosulfide (III).This was reduced with NaBH4 to give a diastereomeric mixture of alcohols (IV).Subsequent oxidation of sulfide group of (IV) with Oxone provided sulfone (V).Condensation with potassium thioacetate under Mitsunobu conditions gave the corresponding thioester as a mixture of isomers,from which the major trans isomer (VI) was isolated by chromatography.Finally,deprotection of (VI) with sodium methoxide in MeOH yielded the target thiol.
合成路线:Michael addition of 4-(phenoxy)thiophenol (II) to cyclohexenone (I) afforded the ketosulfide (III).This was reduced with NaBH4 to give a diastereomeric mixture of alcohols (IV).Subsequent oxidation of sulfide group of (IV) with Oxone provided sulfone (V).Condensation with potassium thioacetate under Mitsunobu conditions gave the corresponding thioester as a mixture of isomers,from which the major trans isomer (VI) was isolated by chromatography.Finally,deprotection of (VI) with sodium methoxide in MeOH yielded the target thiol.
📌 参考资料/链接：
参考文献标题:Synthesis and identification of conformationally constrained selective MMP inhibitors
文献作者:Freskos,J.N.; McDonald,J.J.; Mischke,B.V.; Mullins,P.B.; Shieh,H.S.; Stegeman,R,A.; Stevens,A.M.
参考来源:Bioorg Med Chem Lett 1999,9(13),1757