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【结 构 式】 
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【分子编号】54382 【品名】S-[2-({3-[(tert-butoxycarbonyl)amino]propanoyl}amino)ethyl] ethanethioate 【CA登记号】 |
【 分 子 式 】C12H22N2O4S 【 分 子 量 】290.38376 【元素组成】C 49.64% H 7.64% N 9.65% O 22.04% S 11.04% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of disulfide (I) with sodium azide in DMSO gives the bis azido derivative (II), which is finally reduced with PPh3 in THF/water to afford the target beta-alanine derivative. Alternatively, the condensation of N-(tert-butoxycarbonyl)-beta-alanine (III) with S-acetyl-cysteamine (IV) by means of DCC in ethyl acetate gives the bet-alaninamide (V), which is deacetylated by means of NaOMe in methanol to yield N-[N-(tert-butoxycarbonyl)-beta-alanyl]cysteamine (VI). The dimerization of (VI) by means of I2 in Ac-OH affords the protected cystamine derivative (VII), which is finally deprotected by means of TFA.
| 【1】 Oiry, J.; et al.; Synthesis and radioprotective activity of new cysteamine and cystamine derivatives. J Med Chem 1986, 29, 11, 2217. |
| 【2】 Vogel, K.W.; et al.; Investigating the role of the geminal dimethyl groups of coenzyme A: Synthesis and studies of a didemethyl analogue. Bioorg Med Chem 2000, 8, 10, 2451. |
| 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) | 54379 | 3-chloro-N-[2-({2-[(3-chloropropanoyl)amino]ethyl}disulfanyl)ethyl]propanamide | C10H18Cl2N2O2S2 | 详情 | 详情 | |
| (II) | 54380 | 3-azido-N-[2-({2-[(3-azidopropanoyl)amino]ethyl}disulfanyl)ethyl]propanamide | C10H18N8O2S2 | 详情 | 详情 | |
| (III) | 26616 | N-(tert-butoxycarbonyl)-beta-alanine | 3303-84-2 | C8H15NO4 | 详情 | 详情 |
| (IV) | 54381 | S-(2-aminoethyl) ethanethioate | C4H9NOS | 详情 | 详情 | |
| (V) | 54382 | S-[2-({3-[(tert-butoxycarbonyl)amino]propanoyl}amino)ethyl] ethanethioate | C12H22N2O4S | 详情 | 详情 | |
| (VI) | 54383 | tert-butyl 3-oxo-3-[(2-sulfanylethyl)amino]propylcarbamate | C10H20N2O3S | 详情 | 详情 | |
| (VII) | 54384 | tert-butyl 18,18-dimethyl-3,12,16-trioxo-17-oxa-7,8-dithia-4,11,15-triazanonadec-1-ylcarbamate | C20H38N4O6S2 | 详情 | 详情 |