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【结 构 式】 
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【药物名称】 【化学名称】2-(6-Methoxy-6-pentyl-1,2-dioxan-3-yl)acetic acid methyl ester 【CA登记号】 【 分 子 式 】C13H24O5 【 分 子 量 】260.33323 |
【开发单位】Osaka University (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antimalarials, Treatment of Protozoal Diseases |
合成路线1
Treatment of gamma-butyrolactone (I) with N,O-dimethylhydroxylamine in the presence of dimethylaluminium chloride afforded the corresponding Weinreb amide (II), which was converted to the keto-alcohol (III) by addition of pentylmagnesium bromide. Swern oxidation of alcohol (III), followed by Wittig reaction of the resultant aldehyde (IV) with (methoxycarbonylmethylene)triphenylphosphorane (V), provided the unsaturated keto ester (VI). Subsequent scandium triflate-mediated peroxyhemiacetalyzation of ketone (VI) gave rise to (VII). Then, intramolecular Michael addition of the hydroperoxy ester (VII) in the presence of diethylamine generated the target cyclic peroxide.
| 【1】 Murakami, N.; Horii, T.; Itagaki, S.; Kobayashi, M.; Kawanishi, M.; New readily accessible peroxides with high anti-malarial potency. Bioorg Med Chem Lett 2002, 12, 1, 69. |
| 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) | 20576 | dihydro-2(3H)-furanone | 96-48-0 | C4H6O2 | 详情 | 详情 |
| (II) | 59681 | 4-hydroxy-N-methoxy-N-methylbutanamide | C6H13NO3 | 详情 | 详情 | |
| (III) | 59682 | 1-hydroxy-4-nonanone | C9H18O2 | 详情 | 详情 | |
| (IV) | 59683 | 4-oxononanal | C9H16O2 | 详情 | 详情 | |
| (V) | 14689 | Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane；Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate | 2605-67-6 | C21H19O2P | 详情 | 详情 |
| (VI) | 59684 | methyl (E)-6-oxo-2-undecenoate | C12H20O3 | 详情 | 详情 | |
| (VII) | 59685 | methyl (E)-6-hydroperoxy-6-methoxy-2-undecenoate | C13H24O5 | 详情 | 详情 |