methyl (2S)-2-[((2S,3S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylpentanoyl)amino]-4-(methylsulfanyl)butanoate -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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	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