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【结 构 式】

【分子编号】21226

【品名】(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

【CA登记号】

【 分 子 式 】C32H34BrFO10

【 分 子 量 】677.5183632

【元素组成】C 56.73% H 5.06% Br 11.79% F 2.8% O 23.61%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XII)

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

合成路线2

该中间体在本合成路线中的序号:(XII)

The condensation of (XII) with monosodium pimelate (XIII) in acetone - water yields the protected hemipimelate (XIV), which is finally treated with hot acetic acid - water.

1 Umezawa, H.; Umezawa, S.; Tsuchiya, T.; Takeuchi, T.; Takagi, Y.; Yoneda, T.; Fukatsu, S. (Microbial Chemistry Research Foundation); Novel anthracycline derivs., a process for preparing them and their use as medicaments. EP 0275431; JP 1988141992 .
2 Tsuchiya, T.; Takagi, Y.; Umezawa, S.; Takeuchi, T.; Komuro, K.; Nosaka, C.; Umezawa, H.; Fukatsu, S.; Yoneta, T.; Synthesis and antitumor activities of 14-O-acyl derivatives of 7-O-(2, 6-dideoxy-2-fluoro-alpha-L-talopyranosyl)adriamycin. J Antibiot 1988, 41, 7, 988-91.
3 Hoshi, A.; Prous, J.; Castaner, J.; ME2303. Drugs Fut 1989, 14, 8, 756.
4 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
(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
(XIII) 21227 sodium 6-carboxyhexanoate C7H11NaO4 详情 详情
(XIV) 21228 7-(2-[(2S,4S)-4-[(9-fluoro-3,3,6-trimethylhexahydro-2H,6H-pyrano[3,4-b][1,4]dioxepin-8-yl)oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-2-naphthacenyl]-2-oxoethoxy)-7-oxoheptanoic acid C39H45FO15 详情 详情
Extended Information