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【结 构 式】 
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【分子编号】39959 【品名】(8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-17-glycoloyl-11,16,17-trihydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one 【CA登记号】124-94-7 |
【 分 子 式 】C21H27FO6 【 分 子 量 】394.4401832 【元素组成】C 63.95% H 6.9% F 4.82% O 24.34% |
合成路线1
该中间体在本合成路线中的序号：(I)9alpha,fluoro-11beta16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione (I) is ketalized by reaction with cyclopentanone (II) by means of perchloric acid yielding the ketal (III), which is then acetylated by reaction with acetic anhydride in pyridine.
| 【1】 Hillier, K.; Castaner, J.; Amcinodine. Drugs Fut 1978, 3, 5, 337. |
| 【2】 Sieger, G.M.; Krieger, C. (American Cyanamid Co.); Administration of 16alpha,17alpha-cyclopentylidenedioxy-9alpha-fluoro-11beta,21-dihydroxy-1,4-pregnadiene-3,20-dione-21-acetate. DE 2437847; FR 2240738; GB 1442925; US 4158055 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 39959 | (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-17-glycoloyl-11,16,17-trihydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | 124-94-7 | C21H27FO6 | 详情 | 详情 |
| (II) | 15113 | cyclopentanone | 120-92-3 | C5H8O | 详情 | 详情 |
| (III) | 39960 | triamcinolone cyclopentanonide | 55646-99-6 | C26H33FO6 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The reaction of triamcinolone (I) with acetone and HCl gives the corresponding acetonide (II), which is condensed with glutaric anhydride (III) in pyridine to yield the glutaric monoester (IV). Finally, this compound is condensed with mitomycin C (V) by means of CDI in THF to afford the target conjugate.
| 【1】 Crosson, C.E.; Künzel, E.; Heredia, M.L.; Rix, U.; Oelkers, C.; Rohr, J.; Rohrer, B.; Winberly, M.; Macky, T.A.; Synthesis, pharmacokinetics, efficacy, and rat retinal toxicity of a novel mitomycin C-triamcinolone acetonide conjugate. J Med Chem 2002, 45, 5, 1122. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 39959 | (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-17-glycoloyl-11,16,17-trihydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | 124-94-7 | C21H27FO6 | 详情 | 详情 |
| (II) | 53587 | 5-{2-[(4aS,4bR,5S,6aS,9aR,10aS,10bS)-4b-fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6-yl]-2-oxoethoxy}-5-oxopentanoic acid | n/a | C29H37FO9 | 详情 | 详情 |
| (III) | 15512 | Glutaric Anhydride; dihydro-2H-pyran-2,6(3H)-dione | 108-55-4 | C5H6O3 | 详情 | 详情 |
| (IV) | 53588 | [(1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate | n/a | C15H18N4O5 | 详情 | 详情 |
| (V) | 53589 | 2-Nitro-p-phenetidine; 4-Amino-3-nitrophenetole; 4-Ethoxy-2-nitroaniline; 4-Ethoxy-2-nitrobenzeneamine | 616-86-4 | C8H10N2O3 | 详情 | 详情 |