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Antiviral Powder Trifluridine CAS 70-00-8 For Anti-fection Quick details of Trifluridine powder Product Name: Trifluridine Synonyms: 2,4(1h,3h)-pyrimidinedione,1-(2-deoxy-beta-d-ribofuranosyl)-5-(trifluorometh;Trifluridine (Viroptic);VIROPTIC;
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NewCan Biotech Limited was established in 2021 and is primarily engaged in the research, development, production, and sales of sugars, nucleosides, nucleotides, phosphorylated monomers, as well as next-generation antiviral and antitumor drug intermed
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2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With methanol; sodium methylate at 4 - 6℃; for 3.5h; | 97% |
5-trifluoromethyl-2′-deoxyuridine-3′,5′-diacetate
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With ammonia In methanol at 20℃; | 95% |
With ammonia In methanol at 0 - 20℃; for 16h; | 84% |
With ammonia In methanol at 20℃; for 19h; | 76% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide In water at -3 - 60℃; for 2h; Temperature; Inert atmosphere; | 94.3% |
With tert.-butylhydroperoxide In water at -5 - 65℃; for 3h; Inert atmosphere; Large scale; | 94.8% |
With tert-butyl alcohol In water at 0 - 20℃; for 3h; | 59% |
With mesoporous graphitic carbon nitride In dimethyl sulfoxide at 25℃; Irradiation; | 47% |
With acetone In water at 20℃; for 40h; UV-irradiation; Inert atmosphere; | 44% |
5-(trifluoromethyl)uridine
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
Stage #1: 5-(trifluoromethyl)uridine With sodium hydrogencarbonate; carbonic acid dimethyl ester In N,N-dimethyl-formamide at 120℃; for 8h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 55℃; for 10h; Stage #3: With palladium on activated charcoal; hydrogen; sodium hydroxide In water; N,N-dimethyl-formamide at 15℃; under 4500.45 Torr; for 12h; pH=7 - 8; | 86.4% |
1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-erythro-pentofuranosyl>-5-trifluoromethyluracil
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With sodium methylate In methanol at 20 - 30℃; for 4h; | 82.5% |
With methanol; sodium methylate for 1h; Ambient temperature; | 67% |
3',5'-di-O-acetyl-5-(trifluoromethyl)-2'-deoxyuridine
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With ammonia In methanol for 10h; Ambient temperature; | 82% |
Conditions | Yield |
---|---|
With copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 23h; Inert atmosphere; Sealed tube; regioselective reaction; | 76% |
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide for 24h; Inert atmosphere; Irradiation; | 71% |
With caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation; | 68% |
With iron(III) sulfate; sulfuric acid; dihydrogen peroxide In water; dimethyl sulfoxide at 40 - 50℃; for 0.333333h; | 58% |
5-(trifluoromethyl)-3',5'-di-O-trityl-2'-deoxyuridine
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With formic acid at 0℃; for 0.0166667h; | 40% |
Hexanoic acid (2R,3S,5R)-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-2-hexanoyloxymethyl-tetrahydro-furan-3-yl ester
A
5'-O-hexanoyl-2'-deoxy-5-trifluoromethyluridine
B
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With phosphate buffer In N,N-dimethyl-formamide at 25℃; for 18h; enzym: Pseudomonas fluorescens; | A 62 % Chromat. B 6 % Chromat. |
5-trifluoromethyluracil
thymidine
A
2'-deoxy-5-trifluoromethyluridine
B
thymin
Conditions | Yield |
---|---|
With thymidine phosphorylase from Escherichia coli In phosphate buffer at 35℃; for 2h; pH=7.0; Title compound not separated from byproducts; | A 47 % Chromat. B n/a |
3',5'-di-O-acetyl-2'-deoxyuridine
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 33 percent / XeF2 / 1 h / Ambient temperature 2: 82 percent / NH3 / methanol / 10 h / Ambient temperature View Scheme |
3',5'-di-O-trityl-5-iodo-2'-deoxyuridine
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) copper powder / 1.) HMPA, 120 deg C, 2.5 h, 2.) 45 deg C, 12 h 2: 40 percent / 98percent formic acid / 0.02 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hexamethyldisilazane / 1,2-dichloro-ethane / 0.75 h / Heating 2: 80 percent / zinc chloride / CHCl3 / 15 h / Ambient temperature 3: 67 percent / sodium methoxide, methanol / 1 h / Ambient temperature View Scheme |
5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / zinc chloride / CHCl3 / 15 h / Ambient temperature 2: 67 percent / sodium methoxide, methanol / 1 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
With thymidine phosphorylase In aq. phosphate buffer at 37℃; for 1h; pH=6.8; Enzymatic reaction; |
2'-deoxyuridine
5-trifluoromethyluracil
A
2'-deoxy-5-trifluoromethyluridine
B
uracil
Conditions | Yield |
---|---|
With pyrimidine nucleoside phosphorylase from Bacillus subtilis (E.C. 2.4.2.3) immobilized on Sepabeads EC-EP In aq. phosphate buffer at 20℃; for 10h; pH=7.5; Reagent/catalyst; Enzymatic reaction; |
Conditions | Yield |
---|---|
With immobilized Bacillus psychrosaccharolyticus CECT 4074 nucleoside 2'-deoxyribosyltransferase In aq. phosphate buffer at 37℃; for 2h; pH=7.5; Concentration; Enzymatic reaction; | |
With purine nucleoside phosphorylase; uridine phosphorylase In aq. phosphate buffer; dimethyl sulfoxide at 80℃; for 3h; pH=7; Enzymatic reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 2 h / 20 - 125 °C 2: copper dichloride / chloroform / 24 h / 20 - 30 °C 3: sodium methylate / methanol / 4 h / 20 - 30 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: pyridine / 16 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -60 °C 2.2: 16 h / 20 °C 3.1: copper(l) iodide; potassium fluoride / N,N-dimethyl-formamide / 16 h / 60 °C 3.2: 16 h / 20 °C 4.1: ammonia / methanol / 16 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -60 °C 1.2: 16 h / 20 °C 2.1: copper(l) iodide; potassium fluoride / N,N-dimethyl-formamide / 16 h / 60 °C 2.2: 16 h / 20 °C 3.1: ammonia / methanol / 16 h / 0 - 20 °C View Scheme |
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: copper(l) iodide; potassium fluoride / N,N-dimethyl-formamide / 16 h / 60 °C 1.2: 16 h / 20 °C 2.1: ammonia / methanol / 16 h / 0 - 20 °C View Scheme |
2-deoxy-D-ribose
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: acetyl chloride / 0.5 h / 5 - 10 °C 1.2: 5 h / 5 - 10 °C 2.1: dmap; triethylamine / toluene / 2 h / 25 - 30 °C 3.1: hydrogenchloride; acetyl chloride; acetic acid / 1,4-dioxane; chloroform / 3.25 h / 10 - 15 °C 4.1: 1,1,1,3,3,3-hexamethyl-disilazane; chloro-trimethyl-silane / 3 h / 120 - 125 °C 4.2: 3 h / 25 - 30 °C 5.1: sodium methylate; methanol / 1.5 h / 10 - 15 °C View Scheme |
1-O-methyl-2-deoxy-D-ribofuranoside
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: dmap; triethylamine / toluene / 2 h / 25 - 30 °C 2.1: hydrogenchloride; acetyl chloride; acetic acid / 1,4-dioxane; chloroform / 3.25 h / 10 - 15 °C 3.1: 1,1,1,3,3,3-hexamethyl-disilazane; chloro-trimethyl-silane / 3 h / 120 - 125 °C 3.2: 3 h / 25 - 30 °C 4.1: sodium methylate; methanol / 1.5 h / 10 - 15 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; acetyl chloride; acetic acid / 1,4-dioxane; chloroform / 3.25 h / 10 - 15 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; chloro-trimethyl-silane / 3 h / 120 - 125 °C 2.2: 3 h / 25 - 30 °C 3.1: sodium methylate; methanol / 1.5 h / 10 - 15 °C View Scheme |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
5-trifluoromethyluracil
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 1,1,1,3,3,3-hexamethyl-disilazane; chloro-trimethyl-silane / 3 h / 120 - 125 °C 1.2: 3 h / 25 - 30 °C 2.1: sodium methylate; methanol / 1.5 h / 10 - 15 °C View Scheme |
(2R,3S,5R)-5-(2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidin-1(2H)-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl-4-methylbenzoate
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With methanol; sodium methylate at 10 - 15℃; for 1.5h; Temperature; | 39 g |
[(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: acetonitrile / 3 h / 45 °C 2.1: acetyl chloride; methanol / 10 h / 0 °C 3.1: carbonic acid dimethyl ester; sodium hydrogencarbonate / N,N-dimethyl-formamide / 8 h / 120 °C 3.2: 10 h / 55 °C 3.3: 12 h / 15 °C / 4500.45 Torr / pH 7 - 8 View Scheme |
4,4'-dimethoxytrityl chloride
2'-deoxy-5-trifluoromethyluridine
5'-O-(4,4'-dimethoxytrityl)-α,α,α-trifluorothymidine
Conditions | Yield |
---|---|
With pyridine; dmap at 0 - 20℃; for 21h; | 96% |
With pyridine at 20℃; for 41.5h; Inert atmosphere; | 72% |
With pyridine |
chloro-bis-(2-methoxy-phenyl)-phenyl-methane
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With dmap In pyridine; dichloromethane | 96% |
tert-butyldimethylsilyl chloride
2'-deoxy-5-trifluoromethyluridine
5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-(trifluoromethyl)uridine
Conditions | Yield |
---|---|
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 25℃; for 1h; | 93% |
With pyridine for 12h; Ambient temperature; | 88% |
acetic anhydride
2'-deoxy-5-trifluoromethyluridine
3',5'-di-O-acetyl-5-(trifluoromethyl)-2'-deoxyuridine
Conditions | Yield |
---|---|
dmap In acetonitrile | 92% |
2'-deoxy-5-trifluoromethyluridine
5-carboxy-2'-deoxyuridine
Conditions | Yield |
---|---|
With sodium hydroxide at 37℃; for 36h; pH=10; | 90% |
2'-deoxy-5-trifluoromethyluridine
5'-O-(4,4'-dimethoxytrityl)-α,α,α-trifluorothymidine
Conditions | Yield |
---|---|
With lithium carbonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Heating; | 87% |
Conditions | Yield |
---|---|
With water at 60℃; for 24h; | 84% |
arachidic anhydride
2'-deoxy-5-trifluoromethyluridine
Icosanoic acid (2R,3S,5R)-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-2-icosanoyloxymethyl-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
dmap In acetonitrile | 80% |
3-fluorobenzoic acid anhydride
2'-deoxy-5-trifluoromethyluridine
3',5'-di-O-(m-fluorobenzoyl)-2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
dmap In acetonitrile | 72% |
2'-deoxy-5-trifluoromethyluridine
chloromethyl n-heptanoate
3-n-heptanoyloxymethyl-2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With sodium iodide; potassium carbonate | 71.3% |
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
2'-deoxy-5-trifluoromethyluridine
3',5'-O-TPDS-α,α,α-trifluorothymidine
Conditions | Yield |
---|---|
With pyridine for 3h; Ambient temperature; | 70% |
p-methylbenzoic anhydride
2'-deoxy-5-trifluoromethyluridine
(2R,3S,5R)-5-(2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidin-1(2H)-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl-4-methylbenzoate
Conditions | Yield |
---|---|
dmap In acetonitrile | 68% |
2,3-dihydro-2H-furan
2'-deoxy-5-trifluoromethyluridine
2'-deoxy-3',5'-di-O-(tetrahydro-2-furyl)-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 1,4-dioxane for 0.5h; Ambient temperature; | 67% |
2'-deoxy-5-trifluoromethyluridine
C10H9F3N2O4
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In acetonitrile at -15 - 0℃; for 3.16667h; | 67% |
4-methyl-benzoyl chloride
Hexanoyl chloride
2'-deoxy-5-trifluoromethyluridine
4-Methyl-benzoic acid (2R,3S,5R)-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-2-hexanoyloxymethyl-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
With pyridine | 66% |
n-hexanoic anhydride
2'-deoxy-5-trifluoromethyluridine
Hexanoic acid (2R,3S,5R)-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-2-hexanoyloxymethyl-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
dmap In acetonitrile | 64% |
4-methyl-benzoyl chloride
2'-deoxy-5-trifluoromethyluridine
4-Methyl-benzoic acid (2R,3S,5R)-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
Conditions | Yield |
---|---|
With pyridine | 62% |
capric anhydride
2'-deoxy-5-trifluoromethyluridine
Decanoic acid (2R,3S,5R)-2-decanoyloxymethyl-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
dmap In acetonitrile | 59% |
4-methyl-benzoyl chloride
Hexanoyl chloride
2'-deoxy-5-trifluoromethyluridine
4-Methyl-benzoic acid (2R,3S,5R)-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hexanoyloxy-tetrahydro-furan-2-ylmethyl ester
Conditions | Yield |
---|---|
With pyridine | 57% |
benzoyl chloride
2'-deoxy-5-trifluoromethyluridine
N3-benzoyl-2'-deoxy-5-(trifluoromethyl)uridine
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl acetamide for 12h; Ambient temperature; | 56% |
palmitic anhydride
2'-deoxy-5-trifluoromethyluridine
Hexadecanoic acid (2R,3S,5R)-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-2-hexadecanoyloxymethyl-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
dmap In acetonitrile | 53% |
2'-deoxy-5-trifluoromethyluridine
n-hexadecanoyl chloride
Hexadecanoic acid (2R,3S,5R)-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
Conditions | Yield |
---|---|
With pyridine | 52% |
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