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【结 构 式】 
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【分子编号】17756 【品名】methyl (8S)-8-(bromomethyl)-2-methyl-4-[(1-piperazinylcarbonyl)oxy]-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate 【CA登记号】 |
【 分 子 式 】C31H34BrN5O8 【 分 子 量 】684.54386 【元素组成】C 54.39% H 5.01% Br 11.67% N 10.23% O 18.7% |
合成路线1
该中间体在本合成路线中的序号：(V)A synthesis of [3H]-KW-2189 has been published: The condensation of duocarmycin B2 (I) with tert-butoxycarbonylpiperazine (II) and 4-nitrophenyl chloroformate by means of triethylamine in dichloromethane gives the expected piperazinecarboxylate (III), which is reduced with NaBH4 in allyl alcohol to yield the hydroxy-derivative (IV). The treatment of (IV) with camphorsulfonic acid (CSA) in hot toluene affords the isomerized compound (V) along with simultaneous deprotection of the piperazine ring. Finally, compound (V) is methylated with tritiated methyl iodide and NaHCO3 in acetone/methanol.
| 【1】 Ogasa, T.; Saito, H.; Kinugawa, M.; Nagamura, S.; The synthesis of [H-3]KW-2189, a novel active antitumor antibiotic. J Label Compd Radiopharm 1997, 39, 6, 471. |
| 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) | 17752 | methyl (2S,8S)-8-(bromomethyl)-4-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydropyrrolo[3,2-e]indole-2-carboxylate | C26H26BrN3O8 | 详情 | 详情 | |
| (II) | 13225 | N-tert-Butoxycarbonyl piperazine; tert-butyl 1-piperazinecarboxylate;tert-butyl piperazine-1-carboxylate | 143238-38-4 | C9H18N2O2 | 详情 | 详情 |
| (III) | 17754 | 1-[(2S,8S)-8-(bromomethyl)-2-(methoxycarbonyl)-2-methyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydropyrrolo[3,2-e]indol-4-yl] 4-(tert-butyl) 1,4-piperazinedicarboxylate | C36H42BrN5O11 | 详情 | 详情 | |
| (IV) | 17755 | 1-[(1R,2S,8S)-8-(bromomethyl)-1-hydroxy-2-(methoxycarbonyl)-2-methyl-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydropyrrolo[3,2-e]indol-4-yl] 4-(tert-butyl) 1,4-piperazinedicarboxylate | C36H44BrN5O11 | 详情 | 详情 | |
| (V) | 17756 | methyl (8S)-8-(bromomethyl)-2-methyl-4-[(1-piperazinylcarbonyl)oxy]-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate | C31H34BrN5O8 | 详情 | 详情 |