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【结 构 式】 
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【分子编号】31051 【品名】(2S)-2-[[(cyclopentylsulfanyl)carbonyl]amino]-3,3-dimethylbutyric acid 【CA登记号】 |
【 分 子 式 】C12H21NO3S 【 分 子 量 】259.36968 【元素组成】C 55.57% H 8.16% N 5.4% O 18.51% S 12.36% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The reaction of the protected L-glutamine (I) with N,O-dimethylhydroxylamine (II) by means of isobutyl chloroformate and NMM in dichloromethane gives the methoxyamide (III), which is reduced with DIBAL in THF yielding the glutaminal (IV). The condensation of (IV) with phosphonate (V) by means of NaN(SiMe3)2 in THF affords the carbamoylhexenoate (VI), which is deprotected with TFA and HCl and condensed with N-(tert-butoxycabonyl)-4-methyl-L-phenylalanine (VII) by means of HOBT, NMM and EDC in dichloromethane to give the dipeptide (VIII), which is finally deprotected with HCl and condensed with N-(cyclopentylsulfanylcarbonyl)-L-tert-leucine (IX) by means of HOBT as before.
| 【1】 Webber, S.E.; Dragovich, P.S.; Babine, R.E.; et al.; Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 2. Peptide structure-activity studies. J Med Chem 1998, 41, 15, 2819. |
| 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) | 31045 | (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxo-5-(tritylamino)pentanoic acid | C29H32N2O5 | 详情 | 详情 | |
| (II) | 13361 | (Methoxyamino)methane; N,O-Dimethylhydroxylamine | 1117-97-1 | C2H7NO | 详情 | 详情 |
| (III) | 31046 | tert-butyl (1S)-1-[[methoxy(methyl)amino]carbonyl]-4-oxo-4-(tritylamino)butylcarbamate | C31H37N3O5 | 详情 | 详情 | |
| (IV) | 31047 | tert-butyl (1S)-1-formyl-4-oxo-4-(tritylamino)butylcarbamate | C29H32N2O4 | 详情 | 详情 | |
| (V) | 31048 | ethyl (E,4S)-4-[(tert-butoxycarbonyl)amino]-7-oxo-7-(tritylamino)-2-heptenoate | C33H38N2O5 | 详情 | 详情 | |
| (VI) | 31049 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-methylphenyl)propionic acid | 80102-26-7 | C15H21NO4 | 详情 | 详情 |
| (VII) | 31050 | ethyl (E,4S)-7-amino-4-[[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-methylphenyl)propanoyl]amino]-7-oxo-2-heptenoate | C24H35N3O6 | 详情 | 详情 | |
| (VIII) | 31051 | (2S)-2-[[(cyclopentylsulfanyl)carbonyl]amino]-3,3-dimethylbutyric acid | C12H21NO3S | 详情 | 详情 |