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【结 构 式】

【分子编号】68891

【品名】(2R,3R,4S,6S)-6-(((3aR,4S,7S,8R,9R,10S,11S,13S,15S,15aS)-1-(4-azidobutyl)-10-(((2R,3S,4R,6S)-3-(benzoyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazol-8-yl)oxy)-4-methoxy-2,4-dimethyltetrahydro-2H-pyran-3-yl benzoate

【CA登记号】 

【 分 子 式 】C57H83N5O15

【 分 子 量 】1078.31

【元素组成】C 63.49% H 7.76% N 6.49% O 22.26%

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:(V)

6-O-Methylerythromycin A (I) is protected with benzoic anhydride in the presence of triethylamine and DMAP in ethyl acetate to afford 2’,4”-di-O-benzoyl-6-O-methylerythromycin A (II). Treatment of the protected intermediate (II) with 1,8 diazabicyclo[5.4.0]undec-7-ene (DBU) followed by 1,1-carbonyldiimidazole (CDI) (III) in DMF yields 10,11-anhydro-2’,4”-di-O-benzoyl-12-O-imidazolylcarbonyl-6-Omethylerythromycin A (IV), which is converted to the 2’,4”-di-O-benzoyl-11-N-(4-azidobutyl)-6-O-methylerythromycin A 11,12-cyclic carbamate (V) by treatment with 4-azidobutylamine (XIII) and DBU in DMF. The cladinose sugar is cleaved from carbamate (V) by hydrolysis with 1 N HCl in acetone to provide 11-N-(4-azidobutyl)-5-(2’-benzoyldesosaminyl)-3-hydroxy-6-O-methylerythronolide A 11,12-cyclic carbamate (VI). 1-N-(4-Azidobutyl)-5-(2’-benzoyldesosaminyl)-3-oxo-6-O-methylerythronolide A 11,12-cyclic carbamate (VII) is prepared by oxidation of the secondary alcohol of intermediate (VI) with Dess-Martin periodinane (DMP).

1 Hwang, C., Duffield, J., Chiu, Y. et al. SAR of 11,12-carbamate macrolides/ketolides linked with 1,4-substituted-[1,2,3]-triazoles. 48th Intersci Conf Antimicrob Agents Chemother/Infect Dis Soc Am 46th Annu Meet (Oct 25-28, Washington, DC) 2008, Abst F1-3973.
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) 68888 (3S,4R,5R,6S,7S,9S,11S,12S,13R,14S)-6- (((2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2S,4S,5R,6R)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione   C38H69NO13 详情 详情
(II) 68889 (2R,3R,4S,6S)-6-(((3S,4R,5R,6S,7S,9S,11S,12S,13R,14S)-6-(((2R,3S,4R,6S)-3-(benzoyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxooxacyclotetradecan-4-yl)oxy)-4-methoxy-2,4-dimethyltetrahydro-2H-pyran-3-yl benzoate   C52H77NO15 详情 详情
(III) 11353 1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole) 530-62-1 C7H6N4O 详情 详情
(IV) 68890 (2S,3R,7S,9S,10S,11R,12R,13S)-10-(((2R,3S,4R,6S)-3-(benzoyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-12-(((2S,4S,5R,6R)-5-(benzoyloxy)-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-9-methoxy-3,5,7,9,11,13-hexamethyl-6,14-dioxooxacyclotetradec-4-en-3-yl 1H-imidazole-1-carboxylate   C56H77N3O15 详情 详情
(V) 68891 (2R,3R,4S,6S)-6-(((3aR,4S,7S,8R,9R,10S,11S,13S,15S,15aS)-1-(4-azidobutyl)-10-(((2R,3S,4R,6S)-3-(benzoyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazol-8-yl)oxy)-4-methoxy-2,4-dimethyltetrahydro-2H-pyran-3-yl benzoate   C57H83N5O15 详情 详情
(VI) 68892 (2R,3S,4R,6S)-2-(((3aR,4S,7S,8R,9R,10S,11S,13S,15S,15aS)-1-(4-azidobutyl)-4-ethyl-8-hydroxy-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazol-10-yl)oxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl benzoate   C42H65N5O11 详情 详情
(VII) 68893 (2R,3S,4R,6S)-2-(((3aR,4S,7S,9S,10S,11S,13S,15S,15aS)-1-(4-azidobutyl)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8,14-tetraoxotetradecahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazol-10-yl)oxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl benzoate   C42H63N5O11 详情 详情
(XI) 11883 1,4-Dibromobutane; 1,4-Butylene bromide 110-52-1 C4H8Br2 详情 详情
(XII) 68896 1,4-diazidobutane   C4H8N6 详情 详情
(XIII) 68887 azidobutylamine;4-azidobutan-1-amine   C4H10N4 详情 详情
Extended Information