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【结 构 式】 
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【分子编号】53334 【品名】benzyl 5-[(5-{[5-[(benzyloxy)carbonyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl}-3,4-diethyl-1H-pyrrol-2-yl)methyl]-4-(3-methoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2-carboxylate 【CA登记号】n/a |
【 分 子 式 】C44H51N3O8 【 分 子 量 】749.90436 【元素组成】C 70.47% H 6.85% N 5.6% O 17.07% |
合成路线1
该中间体在本合成路线中的序号：(IX)The condensation of 3-[2-(acetoxymethyl)-5-(benzyloxycarbonyl)-4-methyl-1H-pyrrol-3-yl]propionic acid methyl ester (VII) with 3,4-diethyl-1H-pyrrole (VIII) by means of Ts-OH in ethanol gives the bis adduct (IX). The reduction of both methoxycarbonyl groups of (IX) with borane/THF complex yields bis-propanol derivative (X), which is debenzylated by hydrogenation with H2 and TEA over Pd/C in THF to afford the dicarboxylic acid (XI). The reduction of (XI) with TFA, triethyl orthoformate and LiOH in methanol/water provides the dialdehyde (XII), which is cyclized with the intermediate phenylenediamine (VI) by means of HCl in methanol to give the pentacyclic compound (XIII).
| 【1】 Sessler, J.L.; et al.; Synthesis and structural characterization of lanthanide(III) texaphyrins. Inorg Chem 1993, 32, 14, 3175. |
| 【2】 Sessler, J.L.; Miller, R.A.; Harriman, A.M. (Pharmacyclics, Inc.; University of Texas System); Radiation sensitization using texaphyrins. US 5622946 . |
| 【3】 Sessler, J.L.; Hemmi, G.W.; Magda, D.; Miller, R.A.; Ross, K.L.; Wright, M.; Dow, W.C.; Smith, D.A.; Kral, V.A.; Iverson, B.; Mody, T. (University of Texas System); Texaphyrin metal complex mediated ester hydrolysis. WO 9429316 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 53331 | 2-amino-4,5-bis{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}phenylamine; 4,5-bis{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-1,2-benzenediamine | n/a | C20H36N2O8 | 详情 | 详情 |
| (VII) | 53332 | benzyl 5-[(acetyloxy)methyl]-4-(3-methoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2-carboxylate | n/a | C20H23NO6 | 详情 | 详情 |
| (VIII) | 53333 | 3,4-diethyl-1H-pyrrole | 16200-52-5 | C8H13N | 详情 | 详情 |
| (IX) | 53334 | benzyl 5-[(5-{[5-[(benzyloxy)carbonyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl}-3,4-diethyl-1H-pyrrol-2-yl)methyl]-4-(3-methoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2-carboxylate | n/a | C44H51N3O8 | 详情 | 详情 |
| (X) | 53335 | benzyl 5-[(5-{[5-[(benzyloxy)carbonyl]-3-(3-hydroxypropyl)-4-methyl-1H-pyrrol-2-yl]methyl}-3,4-diethyl-1H-pyrrol-2-yl)methyl]-4-(3-hydroxypropyl)-3-methyl-1H-pyrrole-2-carboxylate | n/a | C42H51N3O6 | 详情 | 详情 |
| (XI) | 53336 | 5-[(5-{[5-carboxy-3-(3-hydroxypropyl)-4-methyl-1H-pyrrol-2-yl]methyl}-3,4-diethyl-1H-pyrrol-2-yl)methyl]-4-(3-hydroxypropyl)-3-methyl-1H-pyrrole-2-carboxylic acid | n/a | C28H39N3O6 | 详情 | 详情 |
| (XII) | 53337 | 5-[(3,4-diethyl-5-{[5-formyl-3-(3-hydroxypropyl)-4-methyl-1H-pyrrol-2-yl]methyl}-1H-pyrrol-2-yl)methyl]-4-(3-hydroxypropyl)-3-methyl-1H-pyrrole-2-carbaldehyde | n/a | C28H39N3O4 | 详情 | 详情 |
| (XIII) | 53338 | 3-[4,5-diethyl-24-(3-hydroxypropyl)-16,17-bis{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-10,23-dimethyl-13,20,25,26,27-pentaazapentacyclo[20.2.1.1~3,6~.1~8,11~.0~14,19~]heptacosa-1(24),3,5,8,10,12,14,16,18,20,22-undecaen-9-yl]-1-propanol | n/a | C48H71N5O10 | 详情 | 详情 |