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【结 构 式】 
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【分子编号】59383 【品名】[(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-9,9a-bis(tetradecanoyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-3-yl]methyl myristate 【CA登记号】 |
【 分 子 式 】C62H106O9 【 分 子 量 】995.51824 【元素组成】C 74.8% H 10.73% O 14.46% |
合成路线1
该中间体在本合成路线中的序号：(III)The acylation of phorbol (I) with tetradecanoyl chloride (II) in pyridine gives the triacyl phorbol (III), which is selective hydrolyzed with NaOMe in methanol at room temperature to yield the monoacyl phorbol (IV). The acylation of (IV) with acetic anhydride in pyridine at 8 C affords the diacetoxy tetradecanoyloxy phorbol (V). Finally, this compound is monodeacetylated by means of HClO4 in methanol at room temperature to provide the target mixed diacylphorbol.
| 【1】 Bresch, H.; et al.; Active components of croton oil. IX. Partial synthesis of the active components of croton oil. Z Naturforsch B - J Chem Sci 1968, 23, 4, 539. |
| 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) | 59382 | (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one | C20H28O6 | 详情 | 详情 | |
| (II) | 30295 | tetradecanoyl chloride | 112-64-1 | C14H27ClO | 详情 | 详情 |
| (III) | 59383 | [(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-9,9a-bis(tetradecanoyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-3-yl]methyl myristate | C62H106O9 | 详情 | 详情 | |
| (IV) | 59384 | (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9a-trihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate | C34H54O7 | 详情 | 详情 | |
| (V) | 59385 | (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-3-[(acetyloxy)methyl]-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate | C38H58O9 | 详情 | 详情 |