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【结 构 式】 
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【分子编号】28272 【品名】(2S)-5-(allyloxy)-2-(decanoylamino)-5-oxopentanoic acid 【CA登记号】 |
【 分 子 式 】C18H31NO5 【 分 子 量 】341.44788 【元素组成】C 63.32% H 9.15% N 4.1% O 23.43% |
合成路线1
该中间体在本合成路线中的序号：(VII)Protection of L-glutamic acid (I) with allyl alcohol and chlorotrimethylsilane produced the gamma-allyl ester (II). Subsequent treatment of (II) with fluorenylmethoxycarbonyl chloride afforded the N-Fmoc derivative (III). This was coupled to Wang resin using EDC and DMAP to provide the glutamate-coupled resin (IV). Removal of the Fmoc protecting group by means of piperidine gave (V), which was then condensed with decanoyl chloride (VI) yielding amide (VII). The allyl ester was then cleaved by treatment with Pd(PPh3)4 and the resulting carboxylic acid (VIII) was coupled with monoprotected diamine (IX) to furnish diamide (X). Deprotection of the allyl carbamate of (X) provided amine (XI).
| 【1】 Wipf, P.; et al.; Combinatorial synthesis and biological evaluation of library of small-molecule Ser/Thr-protein phosphatase inhibitors. Bioorg Med Chem 1997, 5, 1, 165. |
| 【2】 Lazo, J.S.; Rice, R.L.; Cunningham, A.; Wipf, P. (University of Pittsburgh); Phosphatase inhibitors and methods of use thereof. EP 0959884; US 5700821; WO 9804257 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II), (V) | 28269 | (2S)-5-(allyloxy)-2-amino-5-oxopentanoic acid | C8H13NO4 | 详情 | 详情 | |
| (III), (IV) | 28270 | (2S)-5-(allyloxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-oxopentanoic acid | C23H23NO6 | 详情 | 详情 | |
| (I) | 12005 | L-2-Amino propane dicarboxylic acid; (-)-2-Aminoglutaric acid; L-2-Aminopentanoic acid; L-Glutamic acid | 56-86-0 | C5H9NO4 | 详情 | 详情 |
| (V) | 28269 | (2S)-5-(allyloxy)-2-amino-5-oxopentanoic acid | C8H13NO4 | 详情 | 详情 | |
| (VI) | 28271 | decanoyl chloride | 112-13-0 | C10H19ClO | 详情 | 详情 |
| (VII) | 28272 | (2S)-5-(allyloxy)-2-(decanoylamino)-5-oxopentanoic acid | C18H31NO5 | 详情 | 详情 | |
| (VIII) | 28273 | (2S)-2-(decanoylamino)pentanedioic acid | C15H27NO5 | 详情 | 详情 | |
| (IX) | 28274 | allyl 2-(benzylamino)ethylcarbamate | C13H18N2O2 | 详情 | 详情 | |
| (X) | 28275 | (2S)-5-[(2-[[(allyloxy)carbonyl]amino]ethyl)(benzyl)amino]-2-(decanoylamino)-5-oxopentanoic acid | C28H43N3O6 | 详情 | 详情 | |
| (XI) | 28276 | (2S)-5-[(2-aminoethyl)(benzyl)amino]-2-(decanoylamino)-5-oxopentanoic acid | C24H39N3O4 | 详情 | 详情 |