AGN-192093
Chemical Name: 1-Deoxoprostaglandin F2alpha 9,11-O-cyclic carbonate
CAS No. 159359-95-2
项目整合开发状态: Biological Testing
项目研究机构: Allergan (Originator)
合成路线:The esterification of prostaglandin F2alpha (I) with diazomethane in ethyl ether gives the methyl ester (II),which is treated with butylboronic acid in refluxing toluene yielding the cyclic boronate (III).The silylation of (III) with TBDMS triflate and 2,6-lutidine in dichloromethane,with simultaneous cleavage of the boronate affords the monosylilated prostaglandin (IV),which is treated with triphospgene and pyridine in dichloromethane giving the cyclic carbonate (V).The reduction of (V) with LiBH4 in ethyl ether yields the prostanol intermediate (VI),which is finally desilylalted with TBAF in THF.
📌 参考资料/链接：
参考文献标题:7-[Carboxyalkyl or alkenyl]-6-[alkyl or alkenyl]3-oxo-2,4-dioxobicyclo[3.2.1]octane and derivs.thereof
文献作者:Burk,R.M.; Krauss,A.H.; Woodward,D.F.(Allergan,Inc.)
参考来源:EP 0737185; JP 1997507229; US 5416106; WO 9518103
📄 详细内容
合成路线:The esterification of prostaglandin F2alpha (I) with O-benzyl-N,N'-diisopropylisourea (OBIU) in hot toluene gives the benzyl ester (II),which is treated with butylboronic acid in refluxing toluene yielding the cyclic boronate (III).The silylation of (III) with TBDMS triflate and 2,6-lutidine in dichloromethane,with simultaneous cleavage of the boronate affords the monosylilated prostaglandin (IV),which is treated with triphospgene and pyridine in dichloromethane giving the cyclic carbonate (V).The desilyllation of (V) with tetrabutylammonium fluoride (TBAF) in THF intermediate (VI),which is finally reduced with LiBH4 in ethyl ether.
参考文献标题:Synthesis of a novel series of 3-oxo-2,4-dioxobicyclo[3.2.1]octanes: Additional evidence for two thromboxane receptor subtypes
文献作者:Woodward,D.F.; Gibson,L.L.; Gac,T.S.; Krauss,A.H.; Burk,R.M.; Protzman,C.E.; Garst,M.E.
参考来源:Bioorg Med Chem Lett 1994,4(17),2103
产品链接: CAS No. 159359-95-2››