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【结 构 式】 
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【分子编号】21224 【品名】3-(acetoxy)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-5-fluoro-2-methyltetrahydro-2H-pyran-4-yl acetate 【CA登记号】 |
【 分 子 式 】C31H31FO13 【 分 子 量 】630.5777432 【元素组成】C 59.05% H 4.96% F 3.01% O 32.98% |
合成路线1
该中间体在本合成路线中的序号：(X)L-Fucose (I) is converted successively to its methyl glucoside (II), the 3,4-O-isopropylidene derivative (III), the 2-O-acetyl derivative (IV), the 2-O-acetyl-L-methylfucoside (V), the tosylate (VI), the 4-O-benzyl derivative (VII) and finally, through various steps, the 3,4-O-diacetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide (VIII). The condensation of (VIII) with daunomycinone (IX) gives the daunomycin derivative (X), which is converted to the isopropylidene derivative (XI). The bromination of (XI) affords the bromo derivative (XII).
| 【1】 Hoshi, A.; Prous, J.; Castaner, J.; ME2303. Drugs Fut 1989, 14, 8, 756. |
| 【2】 Omoto, S.; Kondo, S.; Fukatsu, S.; Takeuchi, T.; Umezawa, K.; Tsuchiya, T.; Umezawa, S.; Biological properties of ME2303 (FAD-104), a new anthracycline. Drug Exp Clin Res 1988, 14, 7, 435-9. |
| 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) | 21215 | 6-methyltetrahydro-2H-pyran-2,3,4,5-tetrol | C6H12O5 | 详情 | 详情 | |
| (II) | 21216 | 2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol | 14917-55-6 | C7H14O5 | 详情 | 详情 |
| (III) | 21217 | 8-methoxy-3,3,6-trimethylhexahydro-2H,6H-pyrano[3,4-b][1,4]dioxepin-9-ol | C12H22O5 | 详情 | 详情 | |
| (IV) | 21218 | 8-methoxy-3,3,6-trimethylhexahydro-2H,6H-pyrano[3,4-b][1,4]dioxepin-9-yl acetate | C14H24O6 | 详情 | 详情 | |
| (V) | 21219 | 4,5-dihydroxy-2-methoxy-6-methyltetrahydro-2H-pyran-3-yl acetate | C9H16O6 | 详情 | 详情 | |
| (VI) | 21220 | 5-hydroxy-2-methoxy-6-methyl-4-[[(4-methylphenyl)sulfonyl]oxy]tetrahydro-2H-pyran-3-yl acetate | C16H22O8S | 详情 | 详情 | |
| (VII) | 21221 | 5-(acetoxy)-6-methoxy-2-methyl-4-[[(4-methylphenyl)sulfonyl]oxy]tetrahydro-2H-pyran-3-yl 2-phenylacetate | C24H28O9S | 详情 | 详情 | |
| (VIII) | 21222 | 3-(acetoxy)-6-bromo-5-fluoro-2-methyltetrahydro-2H-pyran-4-yl acetate | C10H14BrFO5 | 详情 | 详情 | |
| (IX) | 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 |
| (X) | 21224 | 3-(acetoxy)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-5-fluoro-2-methyltetrahydro-2H-pyran-4-yl acetate | C31H31FO13 | 详情 | 详情 | |
| (XI) | 21225 | (8S,10S)-8-acetyl-10-[(9-fluoro-3,3,6-trimethylhexahydro-2H,6H-pyrano[3,4-b][1,4]dioxepin-8-yl)oxy]-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione | C32H35FO11 | 详情 | 详情 | |
| (XII) | 21226 | (8R,10S)-8-(2-bromoacetyl)-10-[(9-fluoro-3,3,6-trimethylhexahydro-2H,6H-pyrano[3,4-b][1,4]dioxepin-8-yl)oxy]-6,11-dihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione | C32H34BrFO10 | 详情 | 详情 |