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【结 构 式】 
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【分子编号】53704 【品名】N-(3-cyanopropyl)-N-(3-iodopropyl)-4-methylbenzenesulfonamide 【CA登记号】n/a |
【 分 子 式 】C14H19IN2O2S 【 分 子 量 】406.28761 【元素组成】C 41.39% H 4.71% I 31.24% N 6.89% O 7.88% S 7.89% |
合成路线1
该中间体在本合成路线中的序号：(XX)The condensation between 4-bromobutyronitrile (XVI) and 3-amino-1-propanol (XVII) gave the hydroxy amino nitrile (XVIII), which was further converted to the N,O-bis-tosylated derivative (XIX). Displacement of the tosylate ester group of (XIX) with NaI in boiling acetone afforded the alkyl iodide (XX). Alkylation of amine (XV) with iodide (XX) provided the secondary amine adduct (XXI). The p-toluenesulfonamido group of (XXI) was reductively removed by sodium in liquid ammonia, yielding diamine (XXII). Subsequent nitrile reduction by means of LiAlH4 furnished triamine (XXIII).
| 【1】 Moriarty, R.M.; et al.; Synthesis of squalamine. A steroidal antibiotic from the shark. Tetrahedron Lett 1994, 35, 44, 8103. |
| 【2】 Moriarty, R.M.; Guo, L.; Tuladhar, S.M. (Genaera Corp.); Chemical synthesis of squalamine. WO 9419366 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XV) | 53701 | (3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-amino-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-ol | n/a | C33H63NO2Si | 详情 | 详情 |
| (XVI) | 34789 | 4-bromobutanenitrile | 5332-06-9 | C4H6BrN | 详情 | 详情 |
| (XVII) | 18522 | 3-amino-1-propanol | 156-87-6 | C3H9NO | 详情 | 详情 |
| (XVIII) | 53702 | 4-[(3-hydroxypropyl)amino]butanenitrile | n/a | C7H14N2O | 详情 | 详情 |
| (XIX) | 53703 | 3-{(3-cyanopropyl)[(4-methylphenyl)sulfonyl]amino}propyl 4-methylbenzenesulfonate | n/a | C21H26N2O5S2 | 详情 | 详情 |
| (XX) | 53704 | N-(3-cyanopropyl)-N-(3-iodopropyl)-4-methylbenzenesulfonamide | n/a | C14H19IN2O2S | 详情 | 详情 |
| (XXI) | 53705 | N-(3-{[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino}propyl)-N-(3-cyanopropyl)-4-methylbenzenesulfonamide | n/a | C47H81N3O4SSi | 详情 | 详情 |
| (XXII) | 53706 | 4-[(3-{[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino}propyl)amino]butanenitrile | n/a | C40H75N3O2Si | 详情 | 详情 |
| (XXIII) | 53707 | (3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-({3-[(4-aminobutyl)amino]propyl}amino)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-ol | n/a | C40H79N3O2Si | 详情 | 详情 |