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【结 构 式】 
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【分子编号】42339 【品名】(4S)-5-(benzyloxy)-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-oxopentanoic acid 【CA登记号】 |
【 分 子 式 】C27H25NO6 【 分 子 量 】459.49864 【元素组成】C 70.58% H 5.48% N 3.05% O 20.89% |
合成路线1
该中间体在本合成路线中的序号：(VII)D-Phenylglycine (I) was converted to ethyl ester (II) by means of ethanol and thionyl chloride. Coupling of N-Fmoc-S-benzylcysteine (III) with amino ester (II) produced the protected dipeptide (IV). The Fmoc group of (IV) was then removed by treatment with piperidine in DMF to give (V). N-Fmoc-glutamic acid alpha-benzyl ester (VII) was prepared by reaction of glutamic acid alpha-benzyl ester (VI) with N-(fluorenylmethoxycarbonyloxy)succinimide. Coupling of protected glutamic acid (VII) with dipeptide (V) furnished tripeptide (VIII). The Fmoc and ester protecting groups of (VIII) were finally cleaved by treatment with NaOH.
| 【1】 Lyttle, M.H.; et al.; Isozyme-specific glutathione-S-transferase: Design and synthesis. J Med Chem 1994, 37, 1, 189. |
| 【2】 Kauvar, L.M.; Lyttle, M.H. (Telik, Inc.); Glutathione analogs and paralog panels comprising glutathione mimics. EP 0720620; US 5599903; WO 9508563 . |
| 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) | 40170 | (2R)-2-amino-2-phenylethanoic acid | C8H9NO2 | 详情 | 详情 | |
| (II) | 42334 | ethyl (2R)-2-amino-2-phenylethanoate | 17609-48-2 | C10H13NO2 | 详情 | 详情 |
| (III) | 42335 | (2R)-3-(benzylsulfanyl)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid | C25H23NO4S | 详情 | 详情 | |
| (IV) | 42336 | ethyl (2R)-2-[((2R)-3-(benzylsulfanyl)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propanoyl)amino]-2-phenylethanoate | C35H34N2O5S | 详情 | 详情 | |
| (V) | 42337 | ethyl (2R)-2-[[(2R)-2-amino-3-(benzylsulfanyl)propanoyl]amino]-2-phenylethanoate | C20H24N2O3S | 详情 | 详情 | |
| (VI) | 42338 | (4S)-4-amino-5-(benzyloxy)-5-oxopentanoic acid | 13030-09-6 | C12H15NO4 | 详情 | 详情 |
| (VII) | 42339 | (4S)-5-(benzyloxy)-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-oxopentanoic acid | C27H25NO6 | 详情 | 详情 | |
| (VIII) | 42340 | 5-benzyl 13-ethyl (5S,10R,13R)-10-[(benzylsulfanyl)methyl]-1-(9H-fluoren-9-yl)-3,8,11-trioxo-13-phenyl-2-oxa-4,9,12-triazatridecane-5,13-dicarboxylate | C47H47N3O8S | 详情 | 详情 |