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【结 构 式】

【分子编号】16228

【品名】2-((2S,4S)-4-[[(3aR,4S,6R,7R,7aR)-7-fluoro-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-2-naphthacenyl)-2-oxoethyl 3-[(tert-butoxycarbonyl)amino]propanoate

【CA登记号】

【 分 子 式 】C38H44FNO15

【 分 子 量 】773.7635032

【元素组成】C 58.99% H 5.73% F 2.46% N 1.81% O 31.02%

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:(VIII)

Coupling of daunomycinone (III) with 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide (II), which was obtained from 1,3,4-tri-O-acetyl-derivative (I), was performed by a Koenings-Knorr type of reaction to obtain the daunomycin derivative (IV). Deprotection of (IV) with sodium hydroxide in water gave corresponding derivative (V), which was subsequently treated with bromine in dichloromethane and acetone to afford the bromo derivative (VI). Condensation of (VI) with N-Boc-beta-alanine sodium salt (VII) in acetone/water gave the protected beta-alaninate derivative (VIII), which was finally treated with hydrochloride in ether to obtain DA-125.

1 Ok, D.K.; Kim, M.S.; Jung, D.Y. (Dong-A Pharmaceutical Co., Ltd.); L-Talopyranoside derivs. and process for the preparation of same. US 5374746 .
2 Lee, M.G.; Yang, J.; DA-125. Drugs Fut 1996, 21, 8, 782.
3 Tsuchiya, T.; Takagi, Y.; Oka, K.D.; Umezawa, S.; Takeuchi, T.; Wako, N.; Umezawa, H.; Syntheses and antitumor activities of 7-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl)-daunomycinone and adriamycinone. J Antibiot 1986, 39, 11, 731-3.
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) 16221 (2S,3R,4R,5R,6S)-2,5-bis(acetoxy)-3-fluoro-6-methyltetrahydro-2H-pyran-4-yl acetate C12H17FO7 详情 详情
(II) 16222 (2S,3S,4R,5R,6S)-3-(acetoxy)-6-bromo-5-fluoro-2-methyltetrahydro-2H-pyran-4-yl acetate C10H14BrFO5 详情 详情
(III) 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
(IV) 16224 (2S,3R,4R,5R,6R)-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
(V) 16225 (8S,10S)-8-acetyl-10-[[(2R,3R,4R,5S,6S)-3-fluoro-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione C27H27FO11 详情 详情
(VI) 16226 (8S,10S)-10-[[(3aR,4S,6R,7R,7aR)-7-fluoro-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-8-(2-bromoacetyl)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione C30H30BrFO11 详情 详情
(VII) 16227 sodium 3-[(tert-butoxycarbonyl)amino]propanoate C8H14NNaO4 详情 详情
(VIII) 16228 2-((2S,4S)-4-[[(3aR,4S,6R,7R,7aR)-7-fluoro-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-2-naphthacenyl)-2-oxoethyl 3-[(tert-butoxycarbonyl)amino]propanoate C38H44FNO15 详情 详情
(IX) 16229 2-((2S,4S)-4-[[(2R,3R,4R,5S,6S)-3-fluoro-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-2-naphthacenyl)-2-oxoethyl 3-aminopropanoate C30H32FNO13 详情 详情
Extended Information