Taprostene sodium, CG-4203
他前列烯钠 他前列烯 Chemical Name: [(5Z,13E,9alpha,15S)-2,3,4-Trinor-inter-m-phenyl-ene-6,9-epoxy-11,15-dihydroxy-15-cyclohexyl-16,17,18,19,20-pentanor]prosta-5,13-dienoic acid sodium salt; [3aR-[2Z,3aalpha,5alpha(1E,3S*),5beta,6aalpha]]-3-]]4-(3-Cyclohexyl-3-hydroxy-1-propenyl)hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-ylidene]methyl]benzoic acid monosodium salt
CAS No. 87440-45-7, 108945-35-3 (free acid)
项目整合开发状态: Phase III
项目研究机构: Gr黱enthal (Originator)
合成路线:The Wittig condensation of 3alpha,5alpha-bi(trimethylsilyloxy)-2beta-(3-hydroxy-3-cyclohexyl-trans-1-propenyl)cyclopentan-1alpha-acetaldehyde-gamma-lactol (I) with m-carboxyphenylmethyl-triphenylphosphonium bromide (II) by means of butyllithium in DMSO gives 2,3,4-trinor-inter-m-phenylene-9,11,15-trihydroxy-15-cyclohexyl-16,17,18,19,20-pentanorprosta-5,13-dienoic acid (III),which is methylated with diazomethane in ether to the corresponding methyl ester (IV).The reaction of (IV) with I2 and NaHCO3 in ether - water yields the iodinated epoxide (V),which is treated with 1,5-diazabicyclo[4.3.0]non-5-ene in toluene to eliminate HI affording CG-4203 methyl ester (VI).Finally,this compound is saponified with NaOH in methanol - water.
📌 参考资料/链接：
参考文献标题:CG-4203
文献作者:Castar,J.; Hillier,K.; Serradell,M.N.
参考来源:Drugs Fut 1984,9(7),494
📄 详细内容
合成路线:The Wittig condensation of 3alpha,5alpha-bi(trimethylsilyloxy)-2beta-(3-hydroxy-3-cyclohexyl-trans-1-propenyl)cyclopentan-1alpha-acetaldehyde-gamma-lactol (I) with m-carboxyphenylmethyl-triphenylphosphonium bromide (II) by means of butyllithium in DMSO gives 2,3,4-trinor-inter-m-phenylene-9,11,15-trihydroxy-15-cyclohexyl-16,17,18,19,20-pentanorprosta-5,13-dienoic acid (III),which is methylated with diazomethane in ether to the corresponding methyl ester (IV).The reaction of (IV) with I2 and NaHCO3 in ether - water yields the iodinated epoxide (V),which is treated with 1,5-diazabicyclo[4.3.0]non-5-ene in toluene to eliminate HI affording CG-4203 methyl ester (VI).Finally,this compound is saponified with NaOH in methanol - water.
参考文献标题:Heterocyclic prostaglandin type compounds,medicaments containing them and processes for the preparation and use of these heterocyclic compounds and medicaments
文献作者:Seipp,U.; et al.
参考来源:DE 3029984; EP 0045842; JP 57054180; US 4372971
产品链接: CAS No. 87440-45-7›› 产品链接: CAS No.108945-35-3››