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【结 构 式】 
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【分子编号】32739 【品名】L-2-Amino-3-methylpentanoic acid; L-isoleucine 【CA登记号】73-32-5 |
【 分 子 式 】C6H13NO2 【 分 子 量 】131.17476 【元素组成】C 54.94% H 9.99% N 10.68% O 24.39% |
合成路线1
该中间体在本合成路线中的序号：(III)The reaction of disulfide (I) with SOCl2 gives the corresponding acyl chloride (II), which is then condensed with L-isoleucine (III) by means of NaHCO3 in THF.
| 【1】 Fiore, P.J.; et al.; Development and pilot-scale demonstration of a process for inhibitors of the HIV nucleocapsid protein, NCp7. Org Process Res Dev 1998, 2, 3, 151. |
合成路线2
该中间体在本合成路线中的序号：(III)The reaction of disulfide (I) with SOCl2 gives the corresponding acyl chloride (II), which is condensed with L-isoleucine (III) by means of NaHCO3 in THF yielding the disulfide intermediate (IV). Finally, this compound is submitted to an oxidative cyclization with Br2 in acetic acid.
| 【1】 Fiore, P.J.; et al.; Development and pilot-scale demonstration of a process for inhibitors of the HIV nucleocapsid protein, NCp7. Org Process Res Dev 1998, 2, 3, 151. |
| 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) | 26404 | C72H81Br2Cl2IO22S2 | 详情 | 详情 | ||
| (II) | 20405 | 2-[[2-(chlorocarbonyl)phenyl]disulfanyl]benzoyl chloride | C14H8Cl2O2S2 | 详情 | 详情 | |
| (III) | 32739 | L-2-Amino-3-methylpentanoic acid; L-isoleucine | 73-32-5 | C6H13NO2 | 详情 | 详情 |
| (IV) | 32740 | (2S,3S)-2-[(2-[[2-([[(1S,2S)-1-carboxy-2-methylbutyl]amino]carbonyl)phenyl]disulfanyl]benzoyl)amino]-3-methylpentanoic acid | C26H32N2O6S2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)Protection of D-alloisoleucine (I) with Cbz-succinimide afforded benzyl carbamate (II). Activation of the carboxyl group of (II) as the pentafluorophenyl ester (III), followed by condensation with the lithium enolate of methyl acetate, gave beta-ketoester (IV). Stereoselective reduction of (IV) with KBH4 produced alcohol (V) as the major diastereomer. The hydroxyl group of (V) was protected as the triisopropylsilyl ether (VI), and then hydrolysis of the ester group of (VI) yielded carboxylic acid (VII).
| 【1】 Liang, B.; et al.; The first total synthesis of (-)-tamadarin A. Org Lett 1999, 1, 8, 1319. |
| 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) | 32739 | L-2-Amino-3-methylpentanoic acid; L-isoleucine | 73-32-5 | C6H13NO2 | 详情 | 详情 |
| (II) | 23508 | (2S,3S)-2-[[(benzyloxy)carbonyl]amino]-3-methylpentanoic acid | 3160-59-6 | C14H19NO4 | 详情 | 详情 |
| (III) | 37824 | 2,3,4,5,6-pentafluorophenyl (2S,3S)-2-[[(benzyloxy)carbonyl]amino]-3-methylpentanoate | C20H18F5NO4 | 详情 | 详情 | |
| (IV) | 23510 | methyl (4S,5S)-4-[[(benzyloxy)carbonyl]amino]-5-methyl-3-oxoheptanoate | C17H23NO5 | 详情 | 详情 | |
| (V) | 37825 | methyl (3S,4S,5S)-4-[[(benzyloxy)carbonyl]amino]-3-hydroxy-5-methylheptanoate | C17H25NO5 | 详情 | 详情 | |
| (VI) | 37826 | methyl (3S,4S,5S)-4-[[(benzyloxy)carbonyl]amino]-5-methyl-3-[(triisopropylsilyl)oxy]heptanoate | C26H45NO5Si | 详情 | 详情 | |
| (VII) | 37827 | (3S,4S,5S)-4-[[(benzyloxy)carbonyl]amino]-5-methyl-3-[(triisopropylsilyl)oxy]heptanoic acid | C25H43NO5Si | 详情 | 详情 |