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CAS No.: | 760981-83-7 |
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Name: | SOLITHROMYCIN |
Article Data: | 10 |
Molecular Structure: | |
Formula: | C43H65FN6O10 |
Molecular Weight: | 845.022 |
Synonyms: | SOLITHROMYCIN;CEM 101;OP 1068 |
Density: | 1.30±0.1 g/cm3(Predicted) |
Boiling Point: | 969.2±75.0 °C(Predicted) |
PSA: | 197.87000 |
LogP: | 5.12260 |
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 40℃; for 24h; | 98% |
With methanol at 40℃; | 97.7% |
With methanol at 20℃; for 16h; | 0.2 g |
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
Conditions | Yield |
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With Imidazole hydrochloride at 60℃; | 95% |
Stage #1: C36H54FN3O12 at 23℃; under 0.1 Torr; for 12h; Stage #2: 1-(4-aminobutyl)-4-(3-aminophenyl)-1H-1,2,3-triazole With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 45℃; for 2h; | 79 mg |
3-acetylenephenylamine
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
Conditions | Yield |
---|---|
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol for 16h; | 69% |
With copper(l) iodide In toluene at 70℃; for 16h; | 17 mg |
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 24h; | |
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 24h; Reagent/catalyst; Huisgen Cycloaddition; |
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sodium azide / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2.1: hydrogenchloride / methanol; water / 20 h / 20 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 3.2: 2 h / -78 - 20 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 4.2: 2 h / 0 - 20 °C / Inert atmosphere 5.1: methanol / 3 h / Inert atmosphere; Reflux 6.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C View Scheme |
C47H79N5O15
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: hydrogenchloride / methanol; water / 20 h / 20 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 - 20 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 2 h / 0 - 20 °C / Inert atmosphere 4.1: methanol / 3 h / Inert atmosphere; Reflux 5.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C View Scheme |
acetic acid 2-[1-(4-azido-butyl)-4-ethyl-8-hydroxy-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxo-tetradecahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecen-10-yloxy]-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C / Inert atmosphere 3.1: methanol / 3 h / Inert atmosphere; Reflux 4.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C View Scheme |
11-N-(4-azido-butyl)-6-O-methyl-5-(2-acetyl-desosamynyl)-3-oxo-erythronolide A 11,12-carbamate
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: methanol / 3 h / Inert atmosphere; Reflux 3.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C View Scheme |
clarithromycin
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 72 h / 35 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / 48 h / 35 °C / Inert atmosphere 4.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 5.1: sodium azide / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 6.1: hydrogenchloride / methanol; water / 20 h / 20 °C 7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 7.2: 2 h / -78 - 20 °C / Inert atmosphere 8.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 8.2: 2 h / 0 - 20 °C / Inert atmosphere 9.1: methanol / 3 h / Inert atmosphere; Reflux 10.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: triethylamine / ethyl acetate / 24 h / 20 - 25 °C 2.1: hydrogenchloride / water; ethanol / 1.5 h 3.1: pyridine / dichloromethane / 1 h / -20 - 5 °C / Inert atmosphere 4.1: pyridinium chlorochromate / dichloromethane / 24 h / 20 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 24 h / 20 °C 6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -25 - -20 °C / Inert atmosphere 6.2: 1 h / -15 - -10 °C 7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 55 - 65 °C 8.1: potassium tert-butylate / tetrahydrofuran / 1 h / -30 - -20 °C / Inert atmosphere 8.2: 1.5 h / -25 - -20 °C 9.1: N-ethyl-N,N-diisopropylamine; copper(l) iodide / acetonitrile / 20 °C / Inert atmosphere 10.1: methanol / 16 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: triethylamine / ethyl acetate / 24 h / 20 - 25 °C 2.1: hydrogenchloride / water; ethanol / 1.5 h 3.1: pyridine / dichloromethane / 1 h / -20 - 5 °C / Inert atmosphere 4.1: pyridinium chlorochromate / dichloromethane / 24 h / 20 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 24 h / 20 °C 6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -25 - -20 °C / Inert atmosphere 6.2: 1 h / -15 - -10 °C 7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 55 - 60 °C 8.1: pyridine / 2 h / 0 - 10 °C 9.1: sodium azide / N,N-dimethyl-formamide / 8 h / 20 °C 10.1: potassium tert-butylate / tetrahydrofuran / 1 h / -30 - -20 °C / Inert atmosphere 10.2: 1.5 h / -25 - -20 °C 11.1: N-ethyl-N,N-diisopropylamine; copper(l) iodide / acetonitrile / 20 °C / Inert atmosphere 12.1: methanol / 16 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: dmap; triethylamine / ethyl acetate / 16 h / 70 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24.5 h / 28 °C 3.1: hydrogenchloride / acetone; water / 12 h / 40 °C 4.1: dimethylsulfide / dichloromethane / 4 h / -20 °C 4.2: 1.5 h / -20 - 25 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; dimethyl sulfoxide / 24 h / 25 °C 6.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -35 °C 6.2: 2 h / -35 - 25 °C 7.1: hydrogenchloride / water; methanol / 24 h / 40 °C View Scheme |
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
Conditions | Yield |
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Multi-step reaction with 2 steps 1: methanol / 3 h / Inert atmosphere; Reflux 2: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C View Scheme |
2',4''-di-O-acetyl-6-O-methylerythromycin A
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 72 h / 35 °C / Inert atmosphere 2.1: N,N-dimethyl-formamide / 48 h / 35 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 4.1: sodium azide / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 5.1: hydrogenchloride / methanol; water / 20 h / 20 °C 6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 6.2: 2 h / -78 - 20 °C / Inert atmosphere 7.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 7.2: 2 h / 0 - 20 °C / Inert atmosphere 8.1: methanol / 3 h / Inert atmosphere; Reflux 9.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C View Scheme |