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【结 构 式】

【分子编号】27418

【品名】methyl (2S)-2-[((2S,3S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylpentanoyl)amino]-4-(methylsulfanyl)butanoate

【CA登记号】

【 分 子 式 】C17H33N3O4S

【 分 子 量 】375.53284

【元素组成】C 54.37% H 8.86% N 11.19% O 17.04% S 8.54%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

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
Extended Information