药物详细合成路线
| Name | Prostaglandin X sodium;Prostaglandin I2 sodium;Prostacyclin sodium;Epoprostenol sodium;4UA76;U-53217A;Flolan | | Chemical Name | (5Z,9alpha,11alpha,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid sodium salt | | CAS | 61849-14-7 | | Related CAS | 35121-78-9 (free acid) | | Formula | C20H31NaO5 | | Structure |  | | Formula Weight | 374.45687 | | Stage | 上市-1982 | | Company | GlaxoSmithKline (Orphan Drug), GlaxoSmithKline (Originator) | | Activity/Mechanism | Anticoagulants, CARDIOVASCULAR DRUGS, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, Hypertension, Treatment of, Pulmonary Hypertension, Treatment of, Prostacyclin Analogs | | Syn. Route | 1 | | Route 1 | | this compound has been obtained by two similar ways:1) the reaction of 11,15-o-bis(tetrahydropyran-2-yl)prostaglandin f2alpha (i) with nbs in thf/chloroform gives the brominated bicyclic compound (ii), which is treated with acoh to eliminate the thp groups yielding (iii). finally, this compound is deshydrobrominated with potassium tert-butoxide to afford the target compound.2) prostaglandin f2alpha methyl ester (iv) is treated with i2 and k2co3 to give the iodinated bicyclic intermediate (v), which is finally deshydroiodinated with sodium ethoxide to afford the target compound. | | |  | | List of intermediates | No. | | 1-[2-hydroxy-3-propyl-4-[((5z,7e)-8-[(2s,3r)-3-[3-(trifluoromethyl)phenyl]oxiranyl]-5,7-octadienyl)oxy]phenyl]-1-ethanone | (iv) | | allyl 3-(benzyloxy)-5-[[(benzyloxy)methoxy]methyl]-2-(2-[[tert-butyl(dimethyl)silyl]oxy]ethyl)phenylcarbamate | (i) | | 2,2,2-trichloroethyl (4r,5r)-5-[[[(allyloxy)carbonyl]-3-(benzyloxy)-5-[[(benzyloxy)methoxy]methyl]-2-(2-[[tert-butyl(dimethyl)silyl]oxy]ethyl)anilino]methyl]-4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | (ii) | | allyl (2r,3r)-3-amino-4-[[tert-butyl(diphenyl)silyl]oxy]-2-hydroxybutyl[3-(benzyloxy)-5-[[(benzyloxy)methoxy]methyl]-2-(2-[[tert-butyl(dimethyl)silyl]oxy]ethyl)phenyl]carbamate | (iii) | | (1r,2r)-1-[[[(allyloxy)carbonyl]-3-(benzyloxy)-5-[[(benzyloxy)methoxy]methyl]-2-(2-[[tert-butyl(dimethyl)silyl]oxy]ethyl)anilino]methyl]-3-[[tert-butyl(diphenyl)silyl]oxy]-2-[[(4-methylphenyl)sulfonyl]amino]propyl methanesulfonate | (v) | | | Reference 1: hillier, k.; castaner, j.; prostacyclin. drugs fut 1977, 2, 10, 688. Reference 2: nicolaou, k.c.; et al.; rapid and easy preparation of prostacyclin. lancet 1977, 1058. Reference 3: corey, e.j.; et al.; synthesis of vanes prostaglandin x, 6,9alpha-oxidoalpha,15alpha-dihydroxyprosta-(z)5,(e)13-dienoic acid. j am chem soc 1977, 99, 6, 2006. |
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来源:药化网
作者:药化小编
摘要:本文合成路线介绍的是药物中文名依前列醇钠；英文名Prostaglandin X sodium;Prostaglandin I2 sodium;Prostacyclin sodium;Epoprostenol sodium;4UA76;U-53217A;Flolan；CAS[61849-14-7]
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