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【结 构 式】 
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【分子编号】18696 【品名】(8S,10S)-8-acetyl-10-[[(2R,4S,5S,6S)-5-amino-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione 【CA登记号】 |
【 分 子 式 】C27H29NO10 【 分 子 量 】527.528 【元素组成】C 61.47% H 5.54% N 2.66% O 30.33% |
合成路线1
该中间体在本合成路线中的序号：(V)Condensation of daunomycinone (I) with aminoglycal (II) in the presence of triphenylphosphine hydrobromide provided the protected hexopyranosyl daunomycinone (III). Deacetylation with K2CO3 in MeOH-CH2Cl2 gave alcohol (IV), and further hydrolysis of the trifluoroacetamide with NaOH yielded amine (V), which was isolated as the hydrochloride. Finally, condensation of two molecules of (V) with a,a'-dibromo-p-xylene (VI) in the presence of Na2CO3 in DMF-CH2Cl2 at room temperature, followed by precipitation of the dihydrochloride from MeOH-Et2O, provided the target compound.
| 【1】 Priebe, W.; Chaires, J.B.; Przewloka, T.; Fokt, I.; Perez-Soler, R.; Bis-anthracyclines with high activity against doxorubicin resistant tumors. EP 0971716; JP 2000506899; WO 9734612 . |
| 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) | 16223 | (8S,10S)-8-acetyl-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione | 21794-55-8 | C21H18O8 | 详情 | 详情 |
| (II) | 18693 | (2S,3R,4S)-2-methyl-3-[(2,2,2-trifluoroacetyl)amino]-3,4-dihydro-2H-pyran-4-yl acetate | C10H12F3NO4 | 详情 | 详情 | |
| (III) | 18694 | (2S,3R,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-2-methyl-3-[(2,2,2-trifluoroacetyl)amino]tetrahydro-2H-pyran-4-yl acetate | C31H30F3NO12 | 详情 | 详情 | |
| (IV) | 18695 | N-((2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)-2,2,2-trifluoroacetamide | C29H28F3NO11 | 详情 | 详情 | |
| (V) | 18696 | (8S,10S)-8-acetyl-10-[[(2R,4S,5S,6S)-5-amino-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione | C27H29NO10 | 详情 | 详情 | |
| (VI) | 18697 | 1,4-bis(bromomethyl)benzene | 623-24-5 | C8H8Br2 | 详情 | 详情 |