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【结 构 式】

【分子编号】18169

【品名】ethyl 4-methyl-2-[2-(2-naphthylsulfanyl)ethyl]pentanoate

【CA登记号】

【 分 子 式 】C20H26O2S

【 分 子 量 】330.49124

【元素组成】C 72.69% H 7.93% O 9.68% S 9.7%

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:(V)

2-Naphtalenethiol (I) was treated with ethyl 4-bromobutyrate (II) and NaH to give thioether (III). Alkylation of (III) with isobutyl iodide (IV) in the presence of LDA afforded racemic (V), which was then hydrolyzed to the acid (VI) on treatment with litium hydroxide. Coupling of racemic acid (VI) with (S)-leucinol (VII) yielded a mixture of diastereomeric amides, which were separated by column chromatography. Diastereoisomer (VIII) was oxidized with m-chloroperbenzoic acid to give sulfone (IX), and was further oxidized with DMSO and sulfur trioxide-pyridine complex to produce the target aldehyde.

1 Chatterjee, S.; et al.; Nonpeptidic inhibitors of recombinant human calpain; I. Bioorg Med Chem Lett 1997, 7, 3, 287-290.
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) 15234 2-Naphthalenethiol; 2-Naphthylhydrosulfide 91-60-1 C10H8S 详情 详情
(II) 11263 ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate 2969-81-5 C6H11BrO2 详情 详情
(III) 18167 ethyl 4-(2-naphthylsulfanyl)butanoate C16H18O2S 详情 详情
(IV) 18168 1-iodo-2-methylpropane 513-38-2 C4H9I 详情 详情
(V) 18169 ethyl 4-methyl-2-[2-(2-naphthylsulfanyl)ethyl]pentanoate C20H26O2S 详情 详情
(VI) 18170 4-methyl-2-[2-(2-naphthylsulfanyl)ethyl]pentanoic acid C18H22O2S 详情 详情
(VII) 18171 L-(+)-leucinol; (S)-2-amino-4-methyl-1-pentanol; (2S)-2-amino-4-methyl-1-pentanol 7533-40-6 C6H15NO 详情 详情
(VIII) 18172 (2R)-N-[(1S)-1-(hydroxymethyl)-3-methylbutyl]-4-methyl-2-[2-(2-naphthylsulfanyl)ethyl]pentanamide C24H35NO2S 详情 详情
(IX) 18173 (2R)-N-[(1S)-1-(hydroxymethyl)-3-methylbutyl]-4-methyl-2-[2-(2-naphthylsulfonyl)ethyl]pentanamide C24H35NO4S 详情 详情
Extended Information