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【结 构 式】 
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【分子编号】30945 【品名】(2S)-2-[2-(2,6-dimethyl-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)phenoxy]propyl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C32H28N2O6S 【 分 子 量 】568.6502 【元素组成】C 67.59% H 4.96% N 4.93% O 16.88% S 5.64% |
合成路线1
该中间体在本合成路线中的序号：(IX)The condensation of 1-methylindole-2-carbaldehyde (I) with 2-hydroxybenzyl triphenylphosphonium bromide (II) by means of BuLi in THF gives the vinyl derivative (III), which is condensed with (R)(+)-methyl lactate (IV) by means of DEAD and PPh3 in THF yielding the chiral ether derivative (V). The reduction of the carboxylate group of (V) with DIBAL in THF affords the expected chiral propanol derivative (VI), which is cyclized with N-methylmaleimide (VII) by heating at 180 C and aromatized with DDQ giving the pyrrolocarbazole (VIII). The reaction of the hydroxy group of (VIII) with tosyl chloride and pyridine yields the corresponding tosylate (IX), which is finally condensed with dimethylamine in hot DMF.
| 【1】 Ikuina, Y.; et al.; Synthesis and structure-activity relationships of pyrrolocarbazole derivatives possessing thrombopoietic activity. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 089. |
| 【2】 Ikuina, Y.; Murakata, C.; Saitoh, Y.; Shiotsu, Y.; Iida, T.; Tamaoki, T.; Yamashita, K.; Akinaga, S. (Kyowa Hakko Kogyo Co., Ltd.); Pyrrolocarbazole derivs.. EP 0768311; US 5728709; WO 9628447 . |
| 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) | 30938 | 1-methyl-1H-indole-2-carbaldehyde | C10H9NO | 详情 | 详情 | |
| (II) | 30939 | (2-hydroxybenzyl)(triphenyl)phosphonium bromide | 70340-04-4 | C25H22BrOP | 详情 | 详情 |
| (III) | 30940 | 2-[(E)-2-(1-methyl-1H-indol-2-yl)ethenyl]phenol | C17H15NO | 详情 | 详情 | |
| (IV) | 11591 | methyl (2R)-2-hydroxypropanoate | 17392-83-5 | C4H8O3 | 详情 | 详情 |
| (V) | 30941 | methyl (2S)-2-[2-[(E)-2-(1-methyl-1H-indol-2-yl)ethenyl]phenoxy]propanoate | C21H21NO3 | 详情 | 详情 | |
| (VI) | 30942 | (2S)-2-[2-[(E)-2-(1-methyl-1H-indol-2-yl)ethenyl]phenoxy]-1-propanol | C20H21NO2 | 详情 | 详情 | |
| (VII) | 30943 | 1-methyl-1H-pyrrole-2,5-dione | 930-88-1 | C5H5NO2 | 详情 | 详情 |
| (VIII) | 30944 | 4-(2-[[(1S)-2-hydroxy-1-methylethyl]oxy]phenyl)-2,6-dimethylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione | C25H22N2O4 | 详情 | 详情 | |
| (IX) | 30945 | (2S)-2-[2-(2,6-dimethyl-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)phenoxy]propyl 4-methylbenzenesulfonate | C32H28N2O6S | 详情 | 详情 |