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【结 构 式】 
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【药物名称】NSC-262244, TPA 【化学名称】(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-Acetoxy-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-9-(tetradecanoyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one 【CA登记号】16561-29-8, 63597-44-4 (diastereomer) 【 分 子 式 】C36H56O8 【 分 子 量 】616.84292 |
【开发单位】State University of New Jersey (Not Determined) 【药理作用】Leukemia Therapy, Oncolytic Drugs |
合成路线1
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 |