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【结 构 式】 
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【分子编号】18160 【品名】4-chlorophenyl (1R,9S,16S,18S)-16-[(1H-imidazol-1-ylcarbonyl)oxy]-17-oxa-8-azatetracyclo[7.7.2.0(1,18).0(2,7)]octadeca-2,4,6,12-tetraene-10,14-diyne-8-carboxylate 【CA登记号】 |
【 分 子 式 】C27H16ClN3O5 【 分 子 量 】497.89396 【元素组成】C 65.13% H 3.24% Cl 7.12% N 8.44% O 16.07% |
合成路线1
该中间体在本合成路线中的序号：(III)Enediyne compound (I) as an unseparable 2:1 mixture of diastereoisomers was hydrolyzed with barium hydroxide in methanol-dichloromethane at 0 C to provide a mixture of alcohols (II), which were immediately converted into carbonyl imidazole intermediates (III) by treatment with carbonyldiimidazole (CDI) and 4-(dimethylamino)pyridine (DMAP) in cold dichloromethane. Reaction of (III) with an excess of 2-(1-pyrrolidinyl)ethylamine (IV) in dichloromethane at 0 C yielded a 2:1 mixture of diastereoisomeric carbamates, which on treatment with 0.01 M HCl gave the corresponding hydrochlorides.
| 【1】 Unno, R.; et al.; Synthesis and antitumor activity of water-soluble enediyne compounds related to dynemicin A. Bioorg Med Chem 1997, 5, 5, 987-999. |
| 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) | 18158 | 4-chlorophenyl (1R,9S,16S,18S)-16-(acetoxy)-17-oxa-8-azatetracyclo[7.7.2.0(1,18).0(2,7)]octadeca-2,4,6,12-tetraene-10,14-diyne-8-carboxylate | C25H16ClNO5 | 详情 | 详情 | |
| (II) | 18159 | 4-chlorophenyl (1S,9S,16S,18S)-16-hydroxy-17-oxa-8-azatetracyclo[7.7.2.0(1,18).0(2,7)]octadeca-2,4,6,12-tetraene-10,14-diyne-8-carboxylate | C23H14ClNO4 | 详情 | 详情 | |
| (III) | 18160 | 4-chlorophenyl (1R,9S,16S,18S)-16-[(1H-imidazol-1-ylcarbonyl)oxy]-17-oxa-8-azatetracyclo[7.7.2.0(1,18).0(2,7)]octadeca-2,4,6,12-tetraene-10,14-diyne-8-carboxylate | C27H16ClN3O5 | 详情 | 详情 | |
| (IV) | 18161 | 2-(1-pyrrolidinyl)ethylamine; 2-(1-pyrrolidinyl)-1-ethanamine; 1-Pyrrolidineethanamine | 7154-73-6 | C6H14N2 | 详情 | 详情 |