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CAS No.: | 114248-23-6 |
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Name: | 2',2'-DIFLUORO-2'-DEOXYURIDINE |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C9H10 F2 N2 O5 |
Molecular Weight: | 264.186 |
Synonyms: | 2',2'-Difluoro-2'-deoxyuridine;2',2'-Difluorodeoxyuridine; 2'-Deoxy-2',2'-difluorouridine |
Density: | 1.69±0.1 g/cm3(Predicted) |
Melting Point: | 147-149掳C |
PSA: | 104.55000 |
LogP: | -1.57750 |
((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate
Deoxydifluorouridine
Conditions | Yield |
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With ammonia In methanol at 20℃; for 12h; Temperature; | 99% |
With ammonia In methanol | 99% |
With ammonia In methanol at 20℃; for 15h; | 95.8% |
gemcitabine hydrochloride
Deoxydifluorouridine
Conditions | Yield |
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With acetic acid; sodium nitrite In water at 20℃; for 48h; | 95% |
Multi-step reaction with 3 steps 1: pyridine / 15 h / 25 °C 2: acetic acid / water / 14 h / Reflux 3: ammonia / methanol / 15 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: pyridine / 15 h / 25 °C 2: acetic acid / water / 14 h / Reflux 3: ammonia / methanol / 15 h / 20 °C View Scheme |
2'-deoxy-2',2'-difluorouridine-3',5'-dibenzoate
Deoxydifluorouridine
Conditions | Yield |
---|---|
With ammonia In methanol at 23℃; for 23h; | 90% |
gemcitabine
Deoxydifluorouridine
Conditions | Yield |
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With hydrogenchloride; isopentyl nitrite In 1,4-dioxane; water at 70℃; Inert atmosphere; | 68% |
Multi-step reaction with 3 steps 1: dmap; pyridine / 3.5 h / 0 - 20 °C / Inert atmosphere 2: acetic acid / Reflux 3: ammonia / methanol / 20 °C View Scheme |
2’-deoxy-2’,2’-difluoro-cytidine
Deoxydifluorouridine
Conditions | Yield |
---|---|
With water; acetic acid for 24h; Heating; |
gemcitabine hydrochloride
A
Deoxydifluorouridine
B
α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose
Conditions | Yield |
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With sodium hydroxide at 40℃; for 672h; Mechanism; further reagent, temperature, time; |
(2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate
Deoxydifluorouridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetic acid / water / 14 h / Reflux 2: ammonia / methanol / 15 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid / Reflux 2: ammonia / methanol / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid; water / 12 h / 110 °C 2: ammonia / methanol / 12 h / 20 °C View Scheme |
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester
Deoxydifluorouridine
Conditions | Yield |
---|---|
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 20h; Inert atmosphere; diastereoselective reaction; | 87% |
Stage #1: Deoxydifluorouridine With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester In tetrahydrofuran at 0 - 20℃; for 1.5h; |
Conditions | Yield |
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With pyridine; 1H-imidazole at 25 - 50℃; for 12h; Temperature; Inert atmosphere; | 85.5% |
With pyridine; 1H-imidazole at 20℃; | |
With 1H-imidazole In pyridine at 20℃; | |
With 1H-imidazole In N,N-dimethyl-formamide for 8h; Inert atmosphere; |
Deoxydifluorouridine
Conditions | Yield |
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With pyridine; 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere; | 84% |