Solithromycin CAS No.:760981-83-7 Name: Solithromycin Synonyms: CEM 101; OP 1068 Molecular Structure: Molecular Formula: C43H65FN6O10 Molecular Weight: 845.01 CAS Reg
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inquiryAppearance:White to off-white powder Storage:R.T Package:25kg/Barrel Application:A new type of ketolactone (ie macrolide) antibiotic Transportation:Express/Sea/Air Port:Any port in China
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inquiry1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized
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inquiryAbout Product Details Items Specifications Test Results Appearance White to white crystalline powde
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inquiryQingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates, steroids, pharmaceutical
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inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
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inquiryHenan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
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inquiryCompany Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments
Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi
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inquiryProduct Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,
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inquiryfactory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B
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inquiryBOC Sciences is committed to supplying cost-effective products and services. We provide Solithromycin. Solithromycin, also known as CEM-101 and OP-1068, is a ketolide antibiotic undergoing clinical development for the treatment of community-acquire
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(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 |
---|---|
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 |
---|---|
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 |
10,11-anhydro-2',4''-di-O-acetyl-12-O-(imidazol-1-ylcarbonyl)-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 8 steps 1.1: N,N-dimethyl-formamide / 48 h / 35 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 3.1: sodium azide / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 4.1: hydrogenchloride / methanol; water / 20 h / 20 °C 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 5.2: 2 h / -78 - 20 °C / Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 6.2: 2 h / 0 - 20 °C / Inert atmosphere 7.1: methanol / 3 h / Inert atmosphere; Reflux 8.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C View Scheme |
C47H80N2O16
(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 7 steps 1.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 2.1: sodium azide / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; water / 20 h / 20 °C 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 4.2: 2 h / -78 - 20 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 2 h / 0 - 20 °C / Inert atmosphere 6.1: methanol / 3 h / Inert atmosphere; Reflux 7.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C View Scheme |
(R)-3-hydroxy-2-methylpent-1-ene
(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: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C 2.1: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h 3.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C 4.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 5.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 7.1: 130 °C 8.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 8.2: 0.58 h / 23 °C 9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 10.1: 12 h / 23 °C / 0.1 Torr 10.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C 2.1: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h 3.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C 4.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 5.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 7.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 8.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 8.2: 0.58 h / 23 °C 9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 10.1: 12 h / 23 °C / 0.1 Torr 10.2: 2 h / 45 °C View Scheme |
(R)-tert-butyldimethyl((2-methylpent-1-en-3-yl)oxy)silane
(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: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h 2.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C 3.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 4.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 6.1: 130 °C 7.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 7.2: 0.58 h / 23 °C 8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 9.1: 12 h / 23 °C / 0.1 Torr 9.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h 2.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C 3.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 4.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 6.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 7.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 7.2: 0.58 h / 23 °C 8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 9.1: 12 h / 23 °C / 0.1 Torr 9.2: 2 h / 45 °C View Scheme |
(R)-3-((tert-butyldimethylsilyl)oxy)pentan-2-one
(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 8 steps 1.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C 2.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 3.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 5.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 6.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 6.2: 0.58 h / 23 °C 7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 8.1: 12 h / 23 °C / 0.1 Torr 8.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C 2.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 3.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 5.1: 130 °C 6.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 6.2: 0.58 h / 23 °C 7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 8.1: 12 h / 23 °C / 0.1 Torr 8.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 8 steps 1: lithium (1S,2R)-1-phenyl-2-(pyrrolidin-1-yl)-1-propanolate 2: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide 3: Dess-Martin periodane 4: tetrabutyl ammonium fluoride 5: chlorobenzene / 132 °C 6: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 7: 1,8-diazabicyclo[5.4.0]undec-7-ene 8: Imidazole hydrochloride / 60 °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 |
---|---|
Multi-step reaction with 3 steps 1.1: methanol / 24 h / 23 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 2.2: 1 h / -78 °C 3.1: sodium L-ascorbate; copper(II) sulfate / water; tert-butyl alcohol / 16 h View Scheme |
11-N-(4-azido-butyl)-6-O-methyl-5-O-desosaminyl-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 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 1.2: 1 h / -78 °C 2.1: sodium L-ascorbate; copper(II) sulfate / water; tert-butyl alcohol / 16 h 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 |
---|---|
Multi-step reaction with 11 steps 1.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C 1.2: 12 h / -78 °C 2.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve 3.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 5.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 6.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 8.1: 130 °C 9.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 9.2: 0.58 h / 23 °C 10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 11.1: 12 h / 23 °C / 0.1 Torr 11.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C 1.2: 12 h / -78 °C 2.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve 3.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 5.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 6.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 8.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 9.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 9.2: 0.58 h / 23 °C 10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 11.1: 12 h / 23 °C / 0.1 Torr 11.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 11 steps 1: zinc(II) chloride 2: silver trifluoromethanesulfonate 3: hydrogen fluoride / water 4: Dess-Martin periodane 5: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide 6: Dess-Martin periodane 7: tetrabutyl ammonium fluoride 8: chlorobenzene / 132 °C 9: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 10: 1,8-diazabicyclo[5.4.0]undec-7-ene 11: Imidazole hydrochloride / 60 °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 |
---|---|
Multi-step reaction with 6 steps 1.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 3.1: 130 °C 4.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 4.2: 0.58 h / 23 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 6.1: 12 h / 23 °C / 0.1 Torr 6.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 3.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 4.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 4.2: 0.58 h / 23 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 6.1: 12 h / 23 °C / 0.1 Torr 6.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 6 steps 1: Dess-Martin periodane 2: tetrabutyl ammonium fluoride 3: chlorobenzene / 132 °C 4: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 5: 1,8-diazabicyclo[5.4.0]undec-7-ene 6: Imidazole hydrochloride / 60 °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 |
---|---|
Multi-step reaction with 5 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 2.1: 130 °C 3.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 3.2: 0.58 h / 23 °C 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 5.1: 12 h / 23 °C / 0.1 Torr 5.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 2.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 3.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 3.2: 0.58 h / 23 °C 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 5.1: 12 h / 23 °C / 0.1 Torr 5.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 5 steps 1: tetrabutyl ammonium fluoride 2: chlorobenzene / 132 °C 3: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 4: 1,8-diazabicyclo[5.4.0]undec-7-ene 5: Imidazole hydrochloride / 60 °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 |
---|---|
Multi-step reaction with 4 steps 1.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 2.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 2.2: 0.58 h / 23 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 4.1: 12 h / 23 °C / 0.1 Torr 4.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: 130 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 2.2: 0.58 h / 23 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 4.1: 12 h / 23 °C / 0.1 Torr 4.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 4 steps 1: chlorobenzene / 132 °C 2: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 3: 1,8-diazabicyclo[5.4.0]undec-7-ene 4: Imidazole hydrochloride / 60 °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 |
---|---|
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 1.2: 0.58 h / 23 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 3.1: 12 h / 23 °C / 0.1 Torr 3.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 2: 1,8-diazabicyclo[5.4.0]undec-7-ene 3: Imidazole hydrochloride / 60 °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 |
---|---|
Multi-step reaction with 10 steps 1.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve 2.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C 3.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 4.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 5.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 7.1: 130 °C 8.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 8.2: 0.58 h / 23 °C 9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 10.1: 12 h / 23 °C / 0.1 Torr 10.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve 2.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C 3.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 4.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 5.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 7.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 8.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 8.2: 0.58 h / 23 °C 9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 10.1: 12 h / 23 °C / 0.1 Torr 10.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 10 steps 1: silver trifluoromethanesulfonate 2: hydrogen fluoride / water 3: Dess-Martin periodane 4: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide 5: Dess-Martin periodane 6: tetrabutyl ammonium fluoride 7: chlorobenzene / 132 °C 8: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 9: 1,8-diazabicyclo[5.4.0]undec-7-ene 10: Imidazole hydrochloride / 60 °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 |
---|---|
Multi-step reaction with 2 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 2.1: 12 h / 23 °C / 0.1 Torr 2.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene 2: Imidazole hydrochloride / 60 °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 |
---|---|
Multi-step reaction with 4 steps 1.1: tetrabutyl ammonium fluoride / 130 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 2.2: 0.58 h / 23 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 4.1: 12 h / 23 °C / 0.1 Torr 4.2: 2 h / 45 °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 |
---|---|
Multi-step reaction with 9 steps 1.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C 2.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 3.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 4.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 6.1: 130 °C 7.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 7.2: 0.58 h / 23 °C 8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 9.1: 12 h / 23 °C / 0.1 Torr 9.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C 2.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 3.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 4.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 6.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 7.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 7.2: 0.58 h / 23 °C 8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 9.1: 12 h / 23 °C / 0.1 Torr 9.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 9 steps 1: hydrogen fluoride / water 2: Dess-Martin periodane 3: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide 4: Dess-Martin periodane 5: tetrabutyl ammonium fluoride 6: chlorobenzene / 132 °C 7: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 8: 1,8-diazabicyclo[5.4.0]undec-7-ene 9: Imidazole hydrochloride / 60 °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 |
---|---|
Multi-step reaction with 8 steps 1.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 2.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 3.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 5.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 6.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 6.2: 0.58 h / 23 °C 7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 8.1: 12 h / 23 °C / 0.1 Torr 8.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 2.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 3.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 5.1: 130 °C 6.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 6.2: 0.58 h / 23 °C 7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 8.1: 12 h / 23 °C / 0.1 Torr 8.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 8 steps 1: Dess-Martin periodane 2: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide 3: Dess-Martin periodane 4: tetrabutyl ammonium fluoride 5: chlorobenzene / 132 °C 6: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 7: 1,8-diazabicyclo[5.4.0]undec-7-ene 8: Imidazole hydrochloride / 60 °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 |
---|---|
Multi-step reaction with 7 steps 1.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 2.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 4.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 5.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 5.2: 0.58 h / 23 °C 6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 7.1: 12 h / 23 °C / 0.1 Torr 7.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 2.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 4.1: 130 °C 5.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 5.2: 0.58 h / 23 °C 6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 7.1: 12 h / 23 °C / 0.1 Torr 7.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 7 steps 1: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide 2: Dess-Martin periodane 3: tetrabutyl ammonium fluoride 4: chlorobenzene / 132 °C 5: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 6: 1,8-diazabicyclo[5.4.0]undec-7-ene 7: Imidazole hydrochloride / 60 °C View Scheme |
tert-butyl 2-methyl-3-oxopentanoate
(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 13 steps 1.1: acetic anhydride; sulfuric acid / 5 h / 0 - 20 °C 2.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / -78 - 0 °C 2.2: 3 h / -78 - 20 °C 3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C 3.2: 12 h / -78 °C 4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve 5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 10.1: 130 °C 11.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 11.2: 0.58 h / 23 °C 12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 13.1: 12 h / 23 °C / 0.1 Torr 13.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 13 steps 1.1: acetic anhydride; sulfuric acid / 5 h / 0 - 20 °C 2.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / -78 - 0 °C 2.2: 3 h / -78 - 20 °C 3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C 3.2: 12 h / -78 °C 4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve 5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 10.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 11.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 11.2: 0.58 h / 23 °C 12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 13.1: 12 h / 23 °C / 0.1 Torr 13.2: 2 h / 45 °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 |
---|---|
Multi-step reaction with 13 steps 1.1: potassium hydride / diethyl ether; mineral oil / 1 h / 0 °C 1.2: 2 h / 20 °C 2.1: periodic acid / ethyl acetate 3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C 3.2: 12 h / -78 °C 4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve 5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 10.1: 130 °C 11.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 11.2: 0.58 h / 23 °C 12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 13.1: 12 h / 23 °C / 0.1 Torr 13.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 13 steps 1.1: potassium hydride / diethyl ether; mineral oil / 1 h / 0 °C 1.2: 2 h / 20 °C 2.1: periodic acid / ethyl acetate 3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C 3.2: 12 h / -78 °C 4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve 5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C 7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride 8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C 10.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication 11.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C 11.2: 0.58 h / 23 °C 12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C 13.1: 12 h / 23 °C / 0.1 Torr 13.2: 2 h / 45 °C View Scheme | |
Multi-step reaction with 13 steps 1: potassium hydride 2: periodic acid 3: zinc(II) chloride 4: silver trifluoromethanesulfonate 5: hydrogen fluoride / water 6: Dess-Martin periodane 7: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide 8: Dess-Martin periodane 9: tetrabutyl ammonium fluoride 10: chlorobenzene / 132 °C 11: potassium tert-butylate; N-fluorobis(benzenesulfon)imide 12: 1,8-diazabicyclo[5.4.0]undec-7-ene 13: Imidazole hydrochloride / 60 °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 |
---|---|
With di-isopropyl azodicarboxylate In dichloromethane at 20℃; for 24h; | 20% |
(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
trifluoroacetic acid
Conditions | Yield |
---|---|
Stage #1: (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; C103H122N10O20S With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; Stage #2: trifluoroacetic acid In water; acetonitrile | A 16% B 12% |
(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
trifluoroacetic acid
Conditions | Yield |
---|---|
Stage #1: (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; C103H122N10O20S With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Stage #2: trifluoroacetic acid In water-d2; acetonitrile | A 12% B 13% |
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