Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities
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inquiryThe above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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inquiry1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s
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inquiryName (2R)-2-Deoxy-2-fluoro-2-methyl-D-erythropentonic acid gamma-lactone 3,5-dibenzoate Cas 874638-80-9 Appearance: white powder Capacity:20MT/year Application: Sofosbuvir Intermediate Assay: Min99% Standard: enterprise Molecular
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inquiryProduct Name: ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate Synonyms: (2R)-2-DEOXY-2-FLUORO-2-METHYL-D-ERYTHRO;((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl
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inquiryBasic Information Product Name: ((2R,3R,4R)-3-(BENZOYLOXY)-4-FLUORO-4-METHYL-5-OXOTETRAHYDROFURAN-2-YL)METHYL BENZOATE CAS: 874638-80-9
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inquiryAppearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:As
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Min.Order:1 Gram
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Type:Lab/Research institutions
inquiry((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane at 20℃; for 12h; Reagent/catalyst; Solvent; Temperature; Molecular sieve; | 95% |
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane; water at 10 - 20℃; for 2.5h; |
C11H19FO5
benzoyl chloride
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Stage #1: C11H19FO5 With hydrogenchloride In ethanol; water at 20℃; for 22h; Stage #2: benzoyl chloride With pyridine In water; acetonitrile at 0 - 30℃; for 1.16667h; Temperature; | 95% |
benzoyl chloride
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; | 91% |
With triethylamine In dichloromethane at 0 - 20℃; for 3h; | 87% |
With triethylamine In dichloromethane at 0 - 20℃; for 3h; | 87% |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
With triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile Cooling with ice; | 90% |
With fluorosulfonyl fluoride; triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile Cooling with ice; | 87% |
Stage #1: 3,5-dibenzoyl-2-deoxy-2-hydroxy-2-methyl-D-ribose-γ-lactone With triethylamine tris(hydrogen fluoride); triethylamine In ethyl acetate at -17℃; for 1h; Stage #2: With fluorosulfonyl fluoride In ethyl acetate under 750.075 - 3750.38 Torr; Reagent/catalyst; Solvent; Temperature; Cooling; | 87.6% |
Stage #1: 3,5-dibenzoyl-2-deoxy-2-hydroxy-2-methyl-D-ribose-γ-lactone With triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile Stage #2: With potassium chloride In acetonitrile at 0℃; for 2h; | 83% |
(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
benzoyl chloride
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
With pyridine at 20℃; for 0.333333h; | 87% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; | 86% |
With dmap; triethylamine In acetonitrile at 5 - 20℃; for 2h; Temperature; | 84.2% |
3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Stage #1: 3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone With pyridine; trifluoromethylsulfonic anhydride In dichloromethane at -40 - 20℃; for 1h; Stage #2: With fluorosulfonyl fluoride; triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile Cooling with ice; | 78% |
Multi-step reaction with 3 steps 1.1: pyridine / dichloromethane / 0.08 h / -10 °C 1.2: 20 °C 2.1: dichloromethane; water; dimethyl sulfoxide / Cooling with ice 3.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice View Scheme | |
Multi-step reaction with 4 steps 1.1: pyridine / dichloromethane / 0.08 h / -10 °C 1.2: 20 °C 2.1: water / 0.42 h 3.1: triethylamine / water; acetone / 45 °C 4.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice View Scheme |
2-C-methyl-D-ribono-1,4-lactone
benzoyl chloride
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Stage #1: 2-C-methyl-D-ribono-1,4-lactone; benzoyl chloride With triethylamine In dichloromethane Cooling with ice; Stage #2: With pyridine; trifluoromethylsulfonic anhydride In dichloromethane at -40 - 20℃; for 1h; Stage #3: With triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile Cooling with ice; | 58% |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate In 1,4-dioxane for 6h; Solvent; Irradiation; | 52% |
benzoyl chloride
A
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
B
((2R,3R,4S)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methylbenzoate
Conditions | Yield |
---|---|
With pyridine optical yield given as %de; |
benzoyl chloride
A
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
With dmap; triethylamine In acetonitrile at 20 - 40℃; | A 12.7 g B n/a |
(2S,3R)-3-[(4R)-2,2-dimethyl-[1,3]dioxolane-4-yl]-2,3-dihydroxy-2-methylpropionic acid ethyl ester
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: fluorosulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride) / acetonitrile / 5 h / -15 - 90 °C 2: 2,2-dimethoxy-propane; hydrogenchloride; water / tetrahydrofuran / 3 h / 20 °C 3: hydrogenchloride; water / ethanol / 21 h / 20 °C 4: pyridine / 0.5 h / 20 °C / Cooling with ice View Scheme | |
Multi-step reaction with 4 steps 1.1: triethylamine; sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C 2.1: tetraethylammonium fluoride / 1,4-dioxane / 16 h / 120 °C 2.2: 3 h / 20 °C 3.1: water; hydrogenchloride / ethanol / 48 h / 20 °C 4.1: pyridine / 0.75 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: Isopropyl acetate; triethylamine; thionyl chloride / acetonitrile / 1 h / 6 - 9 °C 1.2: 0.5 h 2.1: triethylamine tris(hydrogen fluoride) / 2 h / 82 - 85 °C 3.1: hydrogenchloride / 0.5 h / 90 - 92 °C 3.2: 4 h 4.1: triethylamine; dmap / acetonitrile / 2 h / 5 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: acetic acid / ethanol / 15 h / 80 °C 2.1: pyridine / 2-methyltetrahydrofuran / Inert atmosphere 2.2: 0.5 h / 5 - 15 °C 3.1: triethylamine; triethylamine tris(hydrogen fluoride) / acetonitrile 3.2: 2 h / 0 °C View Scheme |
C10H18O6
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: fluorosulfonyl fluoride; triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene hydrofluoride / acetonitrile / 5 h / 0 - 55 °C 2: 2,2-dimethoxy-propane; water; sulfuric acid / 1,4-dioxane / 16 h / 20 °C / pH 2 - 3 / Cooling with ice 3: hydrogenchloride; water / ethanol / 18 h / 20 °C 4: pyridine / 0.5 h / 20 °C / Cooling with ice View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 2,2-dimethoxy-propane; hydrogenchloride; water / tetrahydrofuran / 3 h / 20 °C 2: hydrogenchloride; water / ethanol / 21 h / 20 °C 3: pyridine / 0.5 h / 20 °C / Cooling with ice View Scheme |
C11H19FO5
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; water / ethanol / 21 h / 20 °C 2: pyridine / 0.5 h / 20 °C / Cooling with ice View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 2,2-dimethoxy-propane; water; sulfuric acid / 1,4-dioxane / 16 h / 20 °C / pH 2 - 3 / Cooling with ice 2: hydrogenchloride; water / ethanol / 18 h / 20 °C 3: pyridine / 0.5 h / 20 °C / Cooling with ice View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; water / ethanol / 18 h / 20 °C 2: pyridine / 0.5 h / 20 °C / Cooling with ice View Scheme |
(S)-3-((2R,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluoro-3-hydroxy-2-methylpropanoyl)-4-benzyloxazolidin-2-one
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 0 - 5 °C 2: triethylamine; dmap / tetrahydrofuran / 2 h / 0 - 40 °C View Scheme |
(S)-3-((2R,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluoro-3-hydroxy-2-methylpropanoyl)-4-isopropyloxazolidin-2-one
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 0 - 5 °C 2: triethylamine; dmap / tetrahydrofuran / 2 h / 0 - 40 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 0 - 5 °C 2: triethylamine; dmap / tetrahydrofuran / 2 h / 0 - 40 °C View Scheme |
C11H18O4
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium permanganate / acetone / 5 h / 0 - 5 °C 2.1: triethylamine; sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C 3.1: tetraethylammonium fluoride / 1,4-dioxane / 16 h / 120 °C 3.2: 3 h / 20 °C 4.1: water; hydrogenchloride / ethanol / 48 h / 20 °C 5.1: pyridine / 0.75 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium hydrogencarbonate; sodium permanganate; ethylene glycol / acetone / 1.5 h / -15 - 10 °C 2.1: Isopropyl acetate; triethylamine; thionyl chloride / acetonitrile / 1 h / 6 - 9 °C 2.2: 0.5 h 3.1: triethylamine tris(hydrogen fluoride) / 2 h / 82 - 85 °C 4.1: hydrogenchloride / 0.5 h / 90 - 92 °C 4.2: 4 h 5.1: triethylamine; dmap / acetonitrile / 2 h / 5 - 20 °C View Scheme |
(4S,5R)-ethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-meth-yl-1,3,2-dioxathiolane-4-carboxylate 2,2-dioxide
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: tetraethylammonium fluoride / 1,4-dioxane / 16 h / 120 °C 1.2: 3 h / 20 °C 2.1: water; hydrogenchloride / ethanol / 48 h / 20 °C 3.1: pyridine / 0.75 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine tris(hydrogen fluoride) / 2 h / 82 - 85 °C 2.1: hydrogenchloride / 0.5 h / 90 - 92 °C 2.2: 4 h 3.1: triethylamine; dmap / acetonitrile / 2 h / 5 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: dmap / toluene / 12 h / 60 °C 2.1: tetraethylammonium fluoride / 1,4-dioxane / 16 h / 105 °C 2.2: 3 h / 20 °C 3.1: ethanol / 1 h / Reflux 4.1: hydrogenchloride / water; ethanol / 22 h / 20 °C 4.2: 1.17 h / 0 - 30 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water; hydrogenchloride / ethanol / 48 h / 20 °C 2: pyridine / 0.75 h / 0 - 20 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dichloromethane; water; dimethyl sulfoxide / Cooling with ice 2: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice View Scheme | |
Multi-step reaction with 3 steps 1: water / 0.42 h 2: triethylamine / water; acetone / 45 °C 3: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice View Scheme | |
Multi-step reaction with 2 steps 1: dimethyl sulfoxide / ethyl acetate 2: triethylamine tris(hydrogen fluoride); triethylamine / acetonitrile / Cooling with ice View Scheme | |
Multi-step reaction with 3 steps 1: 0.5 h / 20 °C 2: triethylamine / acetone / 50 °C 3: triethylamine tris(hydrogen fluoride); triethylamine / acetonitrile / Cooling with ice View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / water; acetone / 45 °C 2: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / acetone / 50 °C 2: triethylamine tris(hydrogen fluoride); triethylamine / acetonitrile / Cooling with ice View Scheme |
benzoyl chloride
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / ethyl acetate / Cooling with ice 2.1: pyridine / dichloromethane / 0.08 h / -10 °C 2.2: 20 °C 3.1: dichloromethane; water; dimethyl sulfoxide / Cooling with ice 4.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice View Scheme | |
Multi-step reaction with 5 steps 1.1: triethylamine / ethyl acetate / Cooling with ice 2.1: pyridine / dichloromethane / 0.08 h / -10 °C 2.2: 20 °C 3.1: water / 0.42 h 4.1: triethylamine / water; acetone / 45 °C 5.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice View Scheme | |
Multi-step reaction with 2 steps 1.1: triethylamine / ethyl acetate / Cooling with ice 2.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 1 h / -40 - 20 °C 2.2: Cooling with ice View Scheme |
2-C-methyl-D-ribono-1,4-lactone
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / ethyl acetate / Cooling with ice 2.1: pyridine / dichloromethane / 0.08 h / -10 °C 2.2: 20 °C 3.1: dichloromethane; water; dimethyl sulfoxide / Cooling with ice 4.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice View Scheme | |
Multi-step reaction with 5 steps 1.1: triethylamine / ethyl acetate / Cooling with ice 2.1: pyridine / dichloromethane / 0.08 h / -10 °C 2.2: 20 °C 3.1: water / 0.42 h 4.1: triethylamine / water; acetone / 45 °C 5.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice View Scheme | |
Multi-step reaction with 2 steps 1.1: triethylamine / ethyl acetate / Cooling with ice 2.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 1 h / -40 - 20 °C 2.2: Cooling with ice View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water; ethanol / 4 h / Reflux 2: triethylamine; dmap / ethyl acetate / 2 h / -5 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: dmap; triethylamine / water; acetonitrile; ethyl acetate / 1 h / 0 - 20 °C / Inert atmosphere; Cooling with ice 1.2: 0.5 h / 0 °C / Inert atmosphere 2.1: Selectfluor / N,N-dimethyl-formamide / 1 h / -40 - 20 °C View Scheme |
methyl iodide
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
With Selectfluor In N,N-dimethyl-formamide at -40 - 20℃; for 1h; | 3.5 g |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetra-(n-butyl)ammonium iodide; potassium nitrite / dimethyl sulfoxide; water / 75 °C 2: triethylamine tris(hydrogen fluoride); triethylamine / acetonitrile / Cooling with ice View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran Inert atmosphere; | 100% |
Stage #1: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at -10 - 0℃; Inert atmosphere; Stage #2: With water; ammonium chloride In tetrahydrofuran Inert atmosphere; | 99% |
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 0℃; for 3h; | 99% |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
Conditions | Yield |
---|---|
With methanesulfonic acid In ethanol for 5h; Reagent/catalyst; Solvent; Reflux; | 95.3% |
With sodium methylate In methanol at 20℃; for 2h; |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene at -10 - -5℃; for 3h; Inert atmosphere; | 90% |
Stage #1: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at -30 - -10℃; for 1.25h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; ethyl acetate at 0℃; | 77% |
With lithium tri(tert-butoxy)aluminum hydride In tetrahydrofuran at -30 - -10℃; for 2.25h; Inert atmosphere; | 77% |
With aluminium In dichloromethane; 2,2,2-trifluoroethanol; toluene at 0 - 10℃; | |
With lithium tri-(tert-butoxy)aluminum hydride In tetrahydrofuran at -20℃; Inert atmosphere; |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at -10 - -5℃; for 3h; Inert atmosphere; | 90% |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Stage #1: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With 2,2,2-trifluoroethanol; sodium bis(2-methoxyethoxy)aluminium dihydride In acetic acid butyl ester; toluene at -20 - -15℃; Stage #2: With sulfuryl dichloride; tetrabutylammomium bromide In acetic acid butyl ester; toluene at -20 - 20℃; | 86% |
Multi-step reaction with 2 steps 1: sodium bis-(2-methoxyethoxy) (2,2,2,trifluoroethoxy) aluminum hydride / toluene; acetic acid butyl ester / -20 - -15 °C 2: tetrabutylammomium bromide; sulfuryl dichloride / toluene; acetic acid butyl ester / 1 h / -20 - 0 °C View Scheme | |
Stage #1: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate In dichloromethane at -10℃; for 0.5h; Stage #2: With sulfuryl dichloride; tetrabutylammomium bromide In dichloromethane at -10 - 20℃; for 16h; |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
7-bromo-2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine
Conditions | Yield |
---|---|
Stage #1: 7-bromo-2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.0833333h; Stage #2: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 2h; | 67% |
Stage #1: 7-bromo-2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 2h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane | 67% |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
(((2R,3R,4R,5R)-3-(benzoyloxy)-5-bromo-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate)
Conditions | Yield |
---|---|
Stage #1: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at -30 - -15℃; for 1.5h; Inert atmosphere; Stage #2: With carbon tetrabromide; triphenylphosphine In tetrahydrofuran; dichloromethane at -20 - 0℃; for 2.16h; Inert atmosphere; | 62% |
With lithium tri-(tert-butoxy)aluminum hydride In tetrahydrofuran; ethyl acetate at -30 - -15℃; for 1.5h; Inert atmosphere; | 62% |
Multi-step reaction with 2 steps 1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.67 h / -30 - -15 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 1.75 h / -20 - -15 °C / Inert atmosphere View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine
Conditions | Yield |
---|---|
Stage #1: 7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.5h; Stage #2: With 1,2-bis-(chlorodimethylsilyl)ethane In tetrahydrofuran for 0.75h; Stage #3: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate Product distribution / selectivity; | 40% |
Stage #1: 7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With 1,2-bis-(chlorodimethylsilyl)ethane In tetrahydrofuran; hexane; water at -78℃; for 3.75h; Inert atmosphere; Stage #3: With ammonium chloride; acetic acid In tetrahydrofuran; hexane Product distribution / selectivity; | 40% |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at -40℃; for 1h; Tebbe Olefination; | 20% |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
7-bromopyrrolo[2,1-f][1,2,4]triazin-4-ylamine
Conditions | Yield |
---|---|
Stage #1: 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-ylamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate In tetrahydrofuran; hexane at -78℃; |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
C27H25FN4O5S2
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C 1.2: 2 h / -78 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
C12H16FN5O3S
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C 1.2: 2 h / -78 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C 3.1: ammonia / 16 h / 50 °C / Sealed tube 3.2: 0.67 h / 60 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
C12H16FN5O5S
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C 1.2: 2 h / -78 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C 3.1: ammonia / 16 h / 50 °C / Sealed tube 3.2: 0.67 h / 60 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
C11H15FN6O3
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C 1.2: 2 h / -78 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C 3.1: ammonia / 16 h / 50 °C / Sealed tube 3.2: 0.67 h / 60 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C 5.1: ammonia / 72 h / 115 °C / Sealed tube View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
C11H14FN5O4
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C 1.2: 2 h / -78 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C 3.1: ammonia / 16 h / 50 °C / Sealed tube 3.2: 0.67 h / 60 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C 5.1: ammonia / 72 h / 115 °C / Sealed tube 6.1: water / bovine spleen type IX sdenosine deaminase A5168 / 4 h / 37 °C / Enzymatic reaction View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
C27H22FN5O5
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C 1.2: 0.75 h 2.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 73 h / 20 - 65 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-carbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C 1.2: 0.75 h 2.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 73 h / 20 - 65 °C 3.1: water; ammonia / methanol / 16 h / 20 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C 1.2: 0.75 h 2.1: water; ammonia / methanol / 16 h / 20 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
C11H17FN5O13P3
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C 1.2: 2 h / -78 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C 3.1: ammonia / 16 h / 50 °C / Sealed tube 3.2: 0.67 h / 60 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C 5.1: ammonia / 72 h / 115 °C / Sealed tube 6.1: water / bovine spleen type IX sdenosine deaminase A5168 / 4 h / 37 °C / Enzymatic reaction 7.1: trichlorophosphate; trimethyl phosphite / 0 °C View Scheme |
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
C25H40FN6O8PS2
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C 1.2: 2 h / -78 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C 3.1: ammonia / 16 h / 50 °C / Sealed tube 3.2: 0.67 h / 60 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C 5.1: ammonia / 72 h / 115 °C / Sealed tube 6.1: 1H-tetrazole; phosphorous acid trimethyl ester / 2 h / 0 °C 7.1: dihydrogen peroxide / water / 0.5 h / 0 - 20 °C View Scheme |
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