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【结 构 式】 
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【分子编号】34609 【品名】(2S,4R)-2-acetyl-2,4,5,12-tetrahydroxy-3,4-dihydro-1,6,11(2H)-naphthacenetrione 【CA登记号】 |
【 分 子 式 】C20H14O8 【 分 子 量 】382.32636 【元素组成】C 62.83% H 3.69% O 33.48% |
合成路线1
该中间体在本合成路线中的序号：(V)The condensation of chiral tetraline (I) with phthalic anhydride (II) by means of AlCl3 at 180 C gives the naphthacenedione (III), which is ketalized at the acetyl group with ethylene glycol and p-toluenesulfonic acid yielding the dioxolane (IV). The hydroxylation of (IV) with Br2 and AIBN in CCl4/CHCl3 affords the 4-demethoxy-7-epidaunomycinone (V), which is isomerized with TFA yielding 4-demethoxydaunomycinone (VI) . The condensation of (VI) with the acylated hexopyranosyl chloride (VII) by means of CF3SO3Ag of Br2Hg affords the trifluoroacetylated 4-demethoxydaunomycin (VIII), which is finally treated with NaOH in order to eliminate the trifluoroacetyl groups
| 【1】 Arcamone, F.; et al.; Synthesis and antitumour activity of new daunorubicin and adriamycin analogues. Experientia 1978, 34, 1255. |
| 【2】 Bernardi, L.; Arcamone, F.; Patelli, B.; Di Marco, A. (Pharmacia Corp.); Daunomycin analogues, their preparation and use. DE 2525633; US 4046878 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 11295 | Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol | 107-21-1 | C2H6O2 | 详情 | 详情 | |
| (I) | 34606 | 1-[(2R)-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenyl]-1-ethanone | C14H18O4 | 详情 | 详情 | |
| (II) | 11900 | 2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride | 85-44-9 | C8H4O3 | 详情 | 详情 |
| (III) | 34607 | (8R)-8-acetyl-6,8,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione | C20H16O6 | 详情 | 详情 | |
| (IV) | 34608 | (8R)-6,8,11-trihydroxy-8-(2-methyl-1,3-dioxolan-2-yl)-7,8,9,10-tetrahydro-5,12-naphthacenedione | C22H20O7 | 详情 | 详情 | |
| (V) | 34609 | (2S,4R)-2-acetyl-2,4,5,12-tetrahydroxy-3,4-dihydro-1,6,11(2H)-naphthacenetrione | C20H14O8 | 详情 | 详情 | |
| (VI) | 34610 | (2S,4S)-2-acetyl-2,4,5,12-tetrahydroxy-3,4-dihydro-1,6,11(2H)-naphthacenetrione | C20H14O8 | 详情 | 详情 | |
| (VII) | 34611 | (2S,3S,4S,6S)-6-chloro-2-methyl-4-[(2,2,2-trifluoroacetyl)amino]tetrahydro-2H-pyran-3-yl 2,2,2-trifluoroacetate | C10H10ClF6NO4 | 详情 | 详情 | |
| (VIII) | 34612 | (3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-4,6,11-trioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-2-methyl-4-[(2,2,2-trifluoroacetyl)amino]tetrahydro-2H-pyran-3-yl 2,2,2-trifluoroacetate | C30H23F6NO12 | 详情 | 详情 |