Flunoprost, ZK-95377
氟诺前列素Chemical Name: (Z)-7-[(1R,2R,3R,5R)-5-Fluoro-3-hydroxy-2-[(E)-(3R)-hydroxy-4-phenoxy-1-butenyl]cyclopentyl]-5-heptenoic acid; (9R,11R,15R)-9-Fluoro-11,15-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-5Z,13E-dienoic acid; 9-Deoxo-9beta-fluoro-16-phenoxy-omega-tetranorprostaglandin E2
CAS No. 86348-98-3
项目整合开发状态: Phase I
项目研究机构: Schering AG (Originator)
合成路线:Esterification of 16-phenoxy-17,18,19-20-tetranor-PGF2alpha-11,15-bistetrahydropyranyl ether (I) with diazomethane followed by fluorination with (diethylamino)sulfur trifluoride (DAST) in the presence of pyridine affords the 9beta-fluoro intermediate (II).Deprotection with acetic acid yields the 11,15-diol (III),which is finally converted to flunoprost by treatment with potassium hydroxide in ethanol - water.
📌 参考资料/链接：
参考文献标题:9-Fluoroprostaglandin derivatives and use as medicinal agents
文献作者:Skuballa,W.; Rad點hel,B.; Schwarz,N.; Vorbr黦gen,H.; Elger,W.; Loge,O.; Town,M.-H.(Schering AG)
参考来源:DE 3126924; EP 0069696; JP 58008059; US 4454339; US 4789685
📄 详细内容
合成路线:Esterification of 16-phenoxy-17,18,19-20-tetranor-PGF2alpha-11,15-bistetrahydropyranyl ether (I) with diazomethane followed by fluorination with (diethylamino)sulfur trifluoride (DAST) in the presence of pyridine affords the 9beta-fluoro intermediate (II).Deprotection with acetic acid yields the 11,15-diol (III),which is finally converted to flunoprost by treatment with potassium hydroxide in ethanol - water.
参考文献标题:N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: Tissue-selective,uterine stimulants
文献作者:Schaaf,T.K.; Bindra,J.S.; Eggler,J.F.; Plattner,J.J.; Nelson,A.J.; Johnson,M.R.; Constantine,J.W.; Hess,H.-J.
参考来源:J Med Chem 1981,24(11),1353-9
合成路线:Esterification of 16-phenoxy-17,18,19-20-tetranor-PGF2alpha-11,15-bistetrahydropyranyl ether (I) with diazomethane followed by fluorination with (diethylamino)sulfur trifluoride (DAST) in the presence of pyridine affords the 9beta-fluoro intermediate (II).Deprotection with acetic acid yields the 11,15-diol (III),which is finally converted to flunoprost by treatment with potassium hydroxide in ethanol - water.
参考文献标题:New fluorinating reagents.Dialkylaminosulfur fluorides
文献作者:Meddleton,W.J.
参考来源:J Org Chem 1975,40574-8
合成路线:Esterification of 16-phenoxy-17,18,19-20-tetranor-PGF2alpha-11,15-bistetrahydropyranyl ether (I) with diazomethane followed by fluorination with (diethylamino)sulfur trifluoride (DAST) in the presence of pyridine affords the 9beta-fluoro intermediate (II).Deprotection with acetic acid yields the 11,15-diol (III),which is finally converted to flunoprost by treatment with potassium hydroxide in ethanol - water.
参考文献标题:FLUNOPROST < Rec INN >
文献作者:Losert,W.; Loge,O.; Beckmann,R.; Skuballa,W.; Thierauch,K.-H.
参考来源:Drugs Fut 1989,14(10),942
产品链接: CAS No. 86348-98-3››