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【结 构 式】

【分子编号】34607

【品名】(8R)-8-acetyl-6,8,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione

【CA登记号】

【 分 子 式 】C20H16O6

【 分 子 量 】352.34344

【元素组成】C 68.18% H 4.58% O 27.25%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

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
Extended Information