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【结 构 式】 
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【分子编号】28478 【品名】4-benzhydryl 2,2-diethyl 5-methyl (4S,5R)-1,3-dioxolane-2,2,4,5-tetracarboxylate 【CA登记号】 |
【 分 子 式 】C25H26O10 【 分 子 量 】486.47544 【元素组成】C 61.72% H 5.39% O 32.89% |
合成路线1
该中间体在本合成路线中的序号：(XIII)Partial hydrolysis of dimethyl D-tartrate (XI), followed by esterification with diphenyldiazomethane provided benzhydryl methyl tartrate (XII). Subsequent condensation of (XII) with diethyl dibromomalonate in the presence of NaH produced dioxolane (XIII). Hydrogenolytic removal of the benzhydryl ester of (XIII) using Pd/C gave carboxylic acid (XIV), which was coupled with the intermediate amine (X) by means of 2-chloro-1,3-dimethylimidazolium chloride (DMC) to furnish amide (XV). Acid hydrolysis of the diethyl acetal of (XV) gave aldehyde (XVI). This was condensed with the benzoxazolylmethyl phosphonium salt (XVII) in the presence of NaH to yield the trans olefin (XVIII). Finally, hydrolysis of the ester groups of (XVIII) with LiOH provided the title tricarboxylic acid.
| 【1】 Aoyama, T.; et al.; A new class of highly potent farnesyl diphosphate-competitive inhibitors of farnesyltransferase. J Med Chem 1998, 41, 2, 143. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 28475 | (2R,3R)-3-(1,3-benzodioxol-5-yl)-5,5-diethoxy-N-(2-naphthylmethyl)-2-pentanamine | C27H33NO4 | 详情 | 详情 | |
| (XI) | 28476 | dimethyl (2S,3S)-2,3-dimethylbutanedioate | C6H10O6 | 详情 | 详情 | |
| (XII) | 28477 | 1-benzhydryl 4-methyl (2S,3S)-2,3-dimethylbutanedioate | C18H18O6 | 详情 | 详情 | |
| (XIII) | 28478 | 4-benzhydryl 2,2-diethyl 5-methyl (4S,5R)-1,3-dioxolane-2,2,4,5-tetracarboxylate | C25H26O10 | 详情 | 详情 | |
| (XIV) | 28479 | (4S,5R)-2,2-bis(ethoxycarbonyl)-5-(methoxycarbonyl)-1,3-dioxolane-4-carboxylic acid | C12H16O10 | 详情 | 详情 | |
| (XV) | 28480 | 2,2-diethyl 4-methyl (4R,5S)-5-[[[(1R,2R)-2-(1,3-benzodioxol-5-yl)-4,4-diethoxy-1-methylbutyl](2-naphthylmethyl)amino]carbonyl]-1,3-dioxolane-2,2,4-tricarboxylate | C39H47NO13 | 详情 | 详情 | |
| (XVI) | 28481 | 2,2-diethyl 4-methyl (4R,5S)-5-[[[(1R,2R)-2-(1,3-benzodioxol-5-yl)-1-methyl-4-oxobutyl](2-naphthylmethyl)amino]carbonyl]-1,3-dioxolane-2,2,4-tricarboxylate | C35H37NO12 | 详情 | 详情 | |
| (XVII) | 28482 | (1,3-benzoxazol-2-ylmethyl)(triphenyl)phosphonium chloride | C26H21ClNOP | 详情 | 详情 | |
| (XVIII) | 28483 | 2,2-diethyl 4-methyl (4R,5S)-5-[[[(1R,2R,4E)-2-(1,3-benzodioxol-5-yl)-5-(1,3-benzoxazol-2-yl)-1-methyl-4-pentenyl](2-naphthylmethyl)amino]carbonyl]-1,3-dioxolane-2,2,4-tricarboxylate | C43H42N2O12 | 详情 | 详情 |