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【结 构 式】 
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【分子编号】38104 【品名】6-hydroxy-7-methyl-1,3-benzodioxole-5-carbaldehyde 【CA登记号】 |
【 分 子 式 】C9H8O4 【 分 子 量 】180.16012 【元素组成】C 60% H 4.48% O 35.52% |
合成路线1
该中间体在本合成路线中的序号：(XXVIII)6-(Benzyloxy)-7-methyl-1,3-benzodioxole-5-carbaldehyde (scheme 13922101a, cp. (I)). The protection of the OH group of phenol (XXIV) with Mom-Br and NaH in DMF/ethyl ether gives the methoxymethyl ether (XXV), which is methylated with MeI and BuLi in hexane yielding the 4-methyl derivative (XXVI). The formylation of (XXVI) with n-BuLi and DMF in THF affords the carbaldehyde (XXVII), which is deprotected with MsOH in dichloromethane giving 6-hydroxy-7-methyl-1,3-benzodioxole-5-carbaldehyde (XXVIII). Finally, this compound is benzylated with benzyl bromide and NaH in DMF providing the desired intermediate (I).
| 【1】 Gin, D.Y.; Corey, E.J.; Kania, R.S.; Enantioselective total synthesis of Ecteinascidin 743. J Am Chem Soc 1996, 118, 38, 9202-03. |
| 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) | 36449 | 6-(benzyloxy)-7-methyl-1,3-benzodioxole-5-carbaldehyde | C16H14O4 | 详情 | 详情 | |
| (XXIV) | 10985 | 1,3-Benzodioxol-5-ol; Sesamol | 533-31-3 | C7H6O3 | 详情 | 详情 |
| (XXV) | 38101 | 1,3-benzodioxol-5-yl methoxymethyl ether; 5-(methoxymethoxy)-1,3-benzodioxole | C9H10O4 | 详情 | 详情 | |
| (XXVI) | 38102 | 5-(methoxymethoxy)-4-methyl-1,3-benzodioxole; methoxymethyl 4-methyl-1,3-benzodioxol-5-yl ether | C10H12O4 | 详情 | 详情 | |
| (XXVII) | 38103 | 6-(methoxymethoxy)-7-methyl-1,3-benzodioxole-5-carbaldehyde | C11H12O5 | 详情 | 详情 | |
| (XXVIII) | 38104 | 6-hydroxy-7-methyl-1,3-benzodioxole-5-carbaldehyde | C9H8O4 | 详情 | 详情 |