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【结 构 式】 
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【分子编号】58015 【品名】octyl (3S)-6-chloro-3-hydroxyhexanoate 【CA登记号】 |
【 分 子 式 】C14H27ClO3 【 分 子 量 】278.81928 【元素组成】C 60.31% H 9.76% Cl 12.72% O 17.21% |
合成路线1
该中间体在本合成路线中的序号：(XXI)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 |