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【结 构 式】

【分子编号】58713

【品名】(2S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid

【CA登记号】

【 分 子 式 】C11H13NO4

【 分 子 量 】223.22856

【元素组成】C 59.19% H 5.87% N 6.27% O 28.67%

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:(II)

The title compound was obtained by solution-phase peptide synthesis. Acylation of L-aspartic acid beta-benzyl ester (II) with the succinimidyl ester of N-Boc-gamma-benzyl-L-glutamic acid (I) led to the protected dipeptide (III). Removal of the Boc protecting group of (III) by means of trifluoroacetic acid afforded amine (IV), which was subsequently condensed with N-Cbz-L-alanine succinimidyl ester (V) to furnish tripeptide (VI). Coupling of (VI) with glycine benzyl ester (VII) using DCC and HOBt gave the fully protected peptide (VIII). The N-Cbz and benzyl ester groups of (VIII) were finally removed by catalytic hydrogenation over Pd/C to provide the target tetrapeptide.

1 Khavinson, V.K.; Tetrapeptide revealing geroprotective effect, pharmacological substance on its basis, and the method of its application. WO 0068255 .
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) 58712 benzyl (4S)-4-[(tert-butoxycarbonyl)amino]-5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxopentanoate C21H26N2O8 详情 详情
(II) 58713 (2S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid C11H13NO4 详情 详情
(III) 58714 (2S)-4-(benzyloxy)-2-({(2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoyl}amino)-4-oxobutanoic acid C28H34N2O9 详情 详情
(IV) 58715 (2S)-2-{[(2S)-2-amino-5-(benzyloxy)-5-oxopentanoyl]amino}-4-(benzyloxy)-4-oxobutanoic acid C23H26N2O7 详情 详情
(V) 27317 benzyl (1S)-2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1-methyl-2-oxoethylcarbamate C15H16N2O6 详情 详情
(VI) 58716 (5S,8S,11S)-11-[2-(benzyloxy)-2-oxoethyl]-8-[3-(benzyloxy)-3-oxopropyl]-5-methyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid C34H37N3O10 详情 详情
(VII) 13601 benzyl 2-aminoacetate; Glycine benzyl ester hydrochloride 1738-68-7 C9H11NO2 详情 详情
(VIII) 58717 benzyl (5S,8S,11S)-11-[2-(benzyloxy)-2-oxoethyl]-8-[3-(benzyloxy)-3-oxopropyl]-5-methyl-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oate C43H46N4O11 详情 详情
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