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【结 构 式】 
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【分子编号】27416 【品名】methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-[[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]sulfanyl]propanoate 【CA登记号】 |
【 分 子 式 】C24H41NO4S 【 分 子 量 】439.65988 【元素组成】C 65.57% H 9.4% N 3.19% O 14.56% S 7.29% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of L-cysteine methyl ester (I) with farnesyl bromide (II) by means of ammonia in methanol gives the S-derivative (III), which is Boc protected as usual yielding the protected cysteine (IV). The reduction of (IV) with diisobutylaluminum hydride in toluene affords the cysteine aldehyde (V), which is reductocondensed with the tripeptide L-valine-L-isoleucine-L-methionine methyl ester (VI) by means of sodium cyanoborohydride in acidic methanol giving the peptide ester (VII). Finally, this compound is hydrolyzed with barium hydroxide in methanol/water.
| 【1】 Rando, R.R. (Harvard College); Cpds. for inhibition of proteolysis. WO 9401126 . |
| 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) | 27413 | methyl (2R)-2-amino-3-sulfanylpropanoate | C4H9NO2S | 详情 | 详情 | |
| (II) | 27414 | (2E,6E)-1-bromo-3,7,11-trimethyl-2,6,10-dodecatriene | C15H25Br | 详情 | 详情 | |
| (III) | 27415 | methyl (2R)-2-amino-3-[[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]sulfanyl]propanoate | C19H33NO2S | 详情 | 详情 | |
| (IV) | 27416 | methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-[[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]sulfanyl]propanoate | C24H41NO4S | 详情 | 详情 | |
| (V) | 27417 | tert-butyl (1R)-1-formyl-2-[[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]sulfanyl]ethylcarbamate | C23H39NO3S | 详情 | 详情 | |
| (VI) | 27418 | methyl (2S)-2-[((2S,3S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylpentanoyl)amino]-4-(methylsulfanyl)butanoate | C17H33N3O4S | 详情 | 详情 | |
| (VII) | 27419 | methyl (6R,9S,12S,15S)-9-isopropyl-2,2-dimethyl-12-[(1S)-1-methylpropyl]-15-[2-(methylsulfanyl)ethyl]-4,10,13-trioxo-6-([[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]sulfanyl]methyl)-3-oxa-5,8,11,14-tetraazahexadecan-16-oate | C40H72N4O6S2 | 详情 | 详情 |