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【结 构 式】

【分子编号】58018

【品名】diethyl 2-{3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl}malonate

【CA登记号】

【 分 子 式 】C15H26O6

【 分 子 量 】302.36784

【元素组成】C 59.58% H 8.67% O 31.75%

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:(XXIV)

In a related method, keto ester (XX) was prepared by Claisen condensation of the lithium enolate of octyl acetate (XVIII) with 4-chlorobutanoyl chloride (XIX). Reduction of the beta-keto ester (XX) with baker's yeast gave rise to the (S)-alcohol (XXI). Subsequent ester group reduction in (XXI) with LiBH4 furnished diol (XXII), which was protected as the acetonide (XXIII) upon treatment with 2,2-dimethoxypropane under acidic conditions. Displacement of the chloride of (XXIII) with the sodium salt of diethyl malonate afforded the substituted malonate (XXIV). Decarbethoxylation of malonate (XXIV) to mono-ester (XXV) was accomplished employing NaCN in hot DMSO. The target dihydroxy ester (XII) was then obtained by acidic acetonide (XXV) hydrolysis.

1 Jacobs, H.K.; Gopalan, A.S.; Bakers' yeast reduction of alkyl 6-chloro-3-oxohexanoates: Synthesis of (R)-(+)-alpha-lipoic acid. J Chem Soc - Perkins Trans I 1990, 7, 1897.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XII) 57958 ethyl (6S)-6,8-dihydroxyoctanoate C10H20O4 详情 详情
(XVIII) 58013 octyl acetate C10H20O2 详情 详情
(XIX) 11265 4-Chlorobutanoyl chloride; 4-Chlorobutyric acid chloride 4635-59-0 C4H6Cl2O 详情 详情
(XX) 58014 octyl 6-chloro-3-oxohexanoate C14H25ClO3 详情 详情
(XXI) 58015 octyl (3S)-6-chloro-3-hydroxyhexanoate C14H27ClO3 详情 详情
(XXII) 58016 (3S)-6-chloro-1,3-hexanediol C6H13ClO2 详情 详情
(XXIII) 58017 (4S)-4-(3-chloropropyl)-2,2-dimethyl-1,3-dioxolane C8H15ClO2 详情 详情
(XXIV) 58018 diethyl 2-{3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl}malonate C15H26O6 详情 详情
(XXV) 58019 ethyl 5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]pentanoate C12H22O4 详情 详情
Extended Information