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【结 构 式】

【分子编号】68895

【品名】(2R,3S,4R,6S)-2-(((3aR,4S,7R,9S,10S,11S,13S,15S,15aS)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-4-ethyl-7-fluoro-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

【CA登记号】 

【 分 子 式 】C50H69FN6O11

【 分 子 量 】949.13

【元素组成】C 63.27% H 7.33% F 2.00% N 8.85% O 18.54%

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:(X)

Fluorination of the keto intermediate (VII) is accomplished with potassium tert-butoxide and N-fluo-robenzenesulfonamide (NFSI) in THF/CH2Cl2 at –20 °C to –15 °C to afford the fluoro-azide intermediate (VIII). The triazole intermediate (X) is prepared by a copper-catalyzed azide-alkyne cycloaddition reaction between the fluoro-azide intermediate (VIII) and 3-ethynylaniline (IX) in the presence of copper(I) iodide and DIEA in acetonitrile. Deprotection of the triazole intermediate (X) is accomplished by refluxing in methanol to yield solithromycin . 4-Azidobutylamine (XIII) is prepared by substitution of 1,4-dibromobutane (XI) with sodium azide in DMF/H2O at 80 °C to produce 1,4-diazidobutane (XII), which, without isolation, is subjected to partial reduction with triphenylphosphine in MTBE to afford 4-azidobutylamine (XIII) .

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
(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
(VIII) 68894 (2R,3S,4R,6S)-2-(((3aR,4S,7R,9S,10S,11S,13S,15S,15aS)-1-(4-azidobutyl)-4-ethyl-7-fluoro-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   C42H62FN5O11 详情 详情
(IX) 56445 3-Aminophenylacetylene; 3-Ethynylaniline; m-Aminophenylacetylene 54060-30-9 C8H7N 详情 详情
(X) 68895 (2R,3S,4R,6S)-2-(((3aR,4S,7R,9S,10S,11S,13S,15S,15aS)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-4-ethyl-7-fluoro-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   C50H69FN6O11 详情 详情
Extended Information