N-((2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-iodo-2-methyltetrahydro-2H-pyran-4-yl)-2,2,2-trifluoroacetamide -Drug Synthesis Database

【结构式】

【分子编号】28762

【品名】N-((2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-iodo-2-methyltetrahydro-2H-pyran-4-yl)-2,2,2-trifluoroacetamide

【CA登记号】

【分子式】C₂₉H₂₇F₃INO₁₀

【分子量】733.4337996

【元素组成】C 47.49% H 3.71% F 7.77% I 17.3% N 1.91% O 21.81%

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 reaction of 4'-epi-N-trifluoroacetyldaunorubicin (I) with trifluoro methanesulfonic anhydride gives the corresponding 4'-O-triflate (II), which is converted to 4'-deoxy-4'-iodo-N-trifluoroacetyldaunorubicin (III). The hydrolysis of (III) with NaOH affords 4'-deoxy-4'-iododaunorubicin (IV), which is finally brominated with Br2 and hydrolyzed with aqueous sodium formate.

参考文献中间体

合成目标

【1】 Suarato, A.; Penco, S.; Casazza, A.M.; Arcamone, F. (Pharmacia Corp.); 4'-Iododerivatives of anthracycline glycosides. BE 0892943; DE 3214559; FR 2525225; GB 2118540; JP 58183698; US 4438105 .
【2】 Suarato, A.; Penco, S.; Arcamone, F. (Pharmacia Corp.); Process for the preparation of 4'-deoxy-daunorubicin and 4'-deoxy-doxorubicin. EP 0048967; IT 1211116; US 4345070 .
【3】 Castaner, R.M.; Serradell, M.N.; Nadhestani, A.N.; Castaner, J.; FCE-21954. Drugs Fut 1987, 12, 9, 849.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	28760	N-Trifluoroacetyldaunomycin; N-((2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-hydroxy-2-methyltetrahydro-2H-pyran-4-yl)-2,2,2-trifluoroacetamide	C₂₉H₂₈F₃NO₁₁	详情	详情
(II)	28761	N-[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-iodo-2-[(trifluoromethyl)sulfonyl]tetrahydro-2H-pyran-4-yl]-2,2,2-trifluoroacetamide	C₂₉H₂₄F₆INO₁₂S	详情	详情
(III)	28762	N-((2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-iodo-2-methyltetrahydro-2H-pyran-4-yl)-2,2,2-trifluoroacetamide	C₂₉H₂₇F₃INO₁₀	详情	详情
(IV)	28763	(8S,10S)-8-acetyl-10-[[(2R,4S,5S,6S)-4-amino-5-iodo-6-methyltetrahydro-2H-pyran-2-yl]oxy]-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione	C₂₇H₂₈INO₉	详情	详情

Extended Information