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【结 构 式】 
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【分子编号】31189 【品名】ethyl (E)-5-(2-chlorophenyl)-4,5-dihydroxy-3-methoxy-2-pentenoate 【CA登记号】 |
【 分 子 式 】C14H17ClO5 【 分 子 量 】300.73868 【元素组成】C 55.91% H 5.7% Cl 11.79% O 26.6% |
合成路线1
该中间体在本合成路线中的序号：(IV)Condensation of 2-chlorobenzaldehyde (I) with methyl 3-methoxy-2(E)-butenoate (II) in the presence of a strong base in dimethyl sulfoxide/water affords, after acidification and reesterification by ethyl bromide/potassium carbonate ethyl 5-(2-chlorophenyl)-3-methyl-2(E),4(E)-pentadienoate (III). Osmium tetroxide catalyzed dihydroxylation of (III) in acetone/water with N-methylmorpholine-N-oxide (NMO) as cooxidant exclusively yields ethyl 5-(2-chlorophenyl)-4,5-threo-dihydroxy-3-methoxy-2(E)-pentenoate (IV), which in acidic medium spontaneously lactonizes to give the parent compound.
| 【1】 Chatterjee, S.S.; Klessing, K. (Willmar Schwabe GmbH); 5-Arylalkyl-4-alkoxy-2(5H)-furanone derivs., intermediates and process for their preparation as well as use as therapeutic agents. DE 3615157; EP 0247320; JP 1988022087; US 4855320 . |
| 【2】 Noldner, M.; Chatterjee, S.S.; LOSIGAMONE < Prop INN >. Drugs Fut 1990, 15, 10, 995. |
| 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) | 24114 | 2-chlorobenzaldehyde | 89-98-5 | C7H5ClO | 详情 | 详情 |
| (II) | 31187 | methyl (E)-3-methoxy-2-butenoate | C6H10O3 | 详情 | 详情 | |
| (III) | 31188 | ethyl (2E,4E)-5-(2-chlorophenyl)-3-methoxy-2,4-pentadienoate | C14H15ClO3 | 详情 | 详情 | |
| (IV) | 31189 | ethyl (E)-5-(2-chlorophenyl)-4,5-dihydroxy-3-methoxy-2-pentenoate | C14H17ClO5 | 详情 | 详情 |