Sch-59761
Chemical Name: N-Ethyl-2-(3-hydroxy-3-phenyl-1-propynyl)adenosine-5'-uronamide
CAS No. 155036-68-3
项目整合开发状态: Preclinical
项目研究机构: Schering-Plough (Originator)
合成路线:2-Iodoadenosine (I) was protected as the ketal (II) on treatment with p-toluenesulfonic in an excess of acetone.This compound was oxidized to the acid (III) with potassium permanganate in aqueous alkaline solution.Deprotection of the ketal was accomplished on heating in 50% formic acid to give IV,which was then esterified in ethanolic solution by means of dropwise addition of thionyl chloride.The resulting ethyl ester (V) was dissolved in liquid ethylamine to afford amide (VI).Finally,VI was coupled with 1-phenyl-2-propyn-1-ol (VII) in the presence of triethylamine and a trace of bis(triphenylphosphine)palladium dichloride and cuprous iodide,to yield the title compound.
📌 参考资料/链接：
参考文献标题:Adenosine derivs.having A2 agonist activity
文献作者:Cristalli,G.(Schering Corp.)
参考来源:US 5593975; WO 9322328
📄 详细内容
合成路线:2-Iodoadenosine (I) was protected as the ketal (II) on treatment with p-toluenesulfonic in an excess of acetone.This compound was oxidized to the acid (III) with potassium permanganate in aqueous alkaline solution.Deprotection of the ketal was accomplished on heating in 50% formic acid to give IV,which was then esterified in ethanolic solution by means of dropwise addition of thionyl chloride.The resulting ethyl ester (V) was dissolved in liquid ethylamine to afford amide (VI).Finally,VI was coupled with 1-phenyl-2-propyn-1-ol (VII) in the presence of triethylamine and a trace of bis(triphenylphosphine)palladium dichloride and cuprous iodide,to yield the title compound.
参考文献标题:2-Alkynyl derivatives of adenosine-5'-N-ethylurona
文献作者:Cristalli,G.; Volpini,R.; Vittori,S.; Camaioni,E.; Monopoli,A.; Conti,A.; Dionisotti,S.; Zocchi,C.; Ongini,E.
参考来源:J Med Chem 1994,37(11),1720