Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 1.5h; detritylation; | 98% |
With iodine(I) bromide In methanol; dichloromethane at 20℃; for 0.0833333h; chemoselective reaction; | 95% |
Stage #1: 5'-O-trityluridine With carbon tetrabromide In methanol for 0.5h; Irradiation; Stage #2: In methanol at 20℃; for 11.5h; | 94% |
Conditions | Yield |
---|---|
With methanol; ammonia at 20℃; | 91% |
With methanol; sodium methylate at 20℃; for 2h; | 87% |
With triethylamine In methanol; water | 83% |
With sodium methylate In methanol Ambient temperature; |
2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine
uridine
Conditions | Yield |
---|---|
With SO3H silica gel In ethyl acetate at 20℃; for 15h; | 81% |
Conditions | Yield |
---|---|
With cytidine deaminase enzyme In aq. phosphate buffer at 37℃; for 0.0833333h; pH=7; Enzymatic reaction; | 99% |
With oxygen; nitrogen(II) oxide In dimethyl sulfoxide for 1h; Ambient temperature; | 47% |
With sodium hydroxide at 90.1℃; Rate constant; Mechanism; various reagent concentration, decomposition to nonchromophoric products; |
Conditions | Yield |
---|---|
With indium(III) triflate In water; acetonitrile at 120℃; for 0.0833333h; Microwave irradiation; | 98% |
With K 10 clay In methanol; water at 75℃; for 26h; | 94% |
With trifluoroacetic acid Yield given; | |
With erbium(III) triflate In water at 120℃; for 0.0833333h; Microwave irradiation; | 99 % Chromat. |
With Pd(OH)2/C; cyclohexene In methanol for 3h; Reflux; |
3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine
uridine
Conditions | Yield |
---|---|
With K 10 clay In methanol; water at 75℃; for 36h; | 97% |
Multi-step reaction with 3 steps 1: 71 percent / triethylamine / 17 h / Ambient temperature 2: 70 percent / 1M tributylammonium fluoride (TBAHF) / tetrahydrofuran / 4 h / Ambient temperature 3: 95 percent / triphenylmethyl fluoroborate / acetonitrile; H2O / 1 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 2 h / 20 °C / Molecular sieve 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h 3: hydrogenchloride; water; lithium iodide / acetonitrile View Scheme |
uridine
Conditions | Yield |
---|---|
With Levalit MDS 1368 cation exchanger (Na-form) In water at 80℃; | 49% |
Conditions | Yield |
---|---|
With methanol; water; triethylamine at 71℃; Microwave irradiation; | 93% |
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 17 h / Ambient temperature 2: 78 percent / conc. NH4OH / methanol 3: 95 percent / triphenylmethyl fluoroborate / acetonitrile; H2O / 1 h / Ambient temperature View Scheme | |
With keratinase from Doratomyces microsporus Hydrolysis; Enzymatic reaction; | |
With ammonia In methanol at 20℃; |
5'-dimethoxytrityluridine
uridine
Conditions | Yield |
---|---|
With K 10 clay In methanol; water at 75℃; for 0.5h; | 96% |
With iodine(I) bromide In methanol; dichloromethane at 20℃; for 0.0166667h; chemoselective reaction; | 95% |
With cerium(IV) triflate; water In acetonitrile at 25℃; for 0.5h; | 93% |
2'-O-allyluridine
uridine
Conditions | Yield |
---|---|
With quinoline-2-carboxylic acid; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In methanol at 30℃; | 99% |
With hexaaquaruthenium(II) tosylate In water at 40℃; for 36h; Time; | 95% |
5'-O-monomethoxytrityluridine
uridine
Conditions | Yield |
---|---|
With sulfuric acid; water; silica gel In acetonitrile at 25℃; for 0.1h; | 90% |
Multi-step reaction with 4 steps 1: tetrahydrofuran / 12 h / Heating 2: 80percent aq. AcOH / 6 h / Ambient temperature 3: 10 percent / triphenylmethyl fluoroborate (TrBF) / acetonitrile; H2O / 2 h / Ambient temperature 4: 94 percent / conc. ammonia, pyridine / 5 h / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: tetrahydrofuran / 12 h / Heating 2: 80percent aq. AcOH / 6 h / Ambient temperature 3: 85 percent / triphenylmethyl fluoroborate (TrBF) / acetonitrile; H2O / 2 h / Ambient temperature View Scheme | |
With hydrogenchloride In water; acetonitrile at 20℃; for 1h; pH=Ca. 1; Inert atmosphere; | 76 mg |
uridine
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 55℃; for 1h; Sealed tube; | |
With tetra-n-butylammonium halide In dimethylsulfoxide-d6 at 55℃; Sealed tube; |
2′,3′-O-bis-(benzyloxycarbonyl)uridine
uridine
Conditions | Yield |
---|---|
With cyclohexa-1,4-diene; palladium on activated charcoal In N,N-dimethyl-formamide for 1.5h; | 99% |
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; E. coli purine nucleoside phosphorylase; E. coli uridine phosphorylase In aq. buffer at 20℃; for 20h; pH=7.5; Enzymatic reaction; | 27 %Chromat. |
3',5'-bis-O-(tert-butyldimethylsilyl)uridine
uridine
Conditions | Yield |
---|---|
With cyclohexene; trimethyleneglycol In methanol for 6h; Heating; | 100% |
With ammonium fluoride In methanol at 60℃; | |
Multi-step reaction with 2 steps 1: cyclohexene / PdO / methanol / Heating 2: cyclohexene / PdO / methanol / Heating View Scheme |
uridine
Conditions | Yield |
---|---|
With ammonium chloride; zinc In methanol at 20℃; for 2h; |
uridine
Conditions | Yield |
---|---|
With ammonium chloride; zinc In methanol at 20℃; |
Conditions | Yield |
---|---|
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Irradiation; chemoselective reaction; | 98% |
Conditions | Yield |
---|---|
With zinc(II) nitrate; sodium nitrate; HEPES buffer In water at 90.1℃; Rate constant; | |
With triethanolamine; potassium chloride; water; m-bis(guanidinomethyl)benzene at 80℃; pH=7.5; Kinetics; Further Variations:; Catalysts; Hydrolysis; | |
With (Zn(2+))2*1,4-bis[(1,5,9-triazacyclododecan-3-yloxy)Me]C6H4 In various solvent(s) at 90℃; pH=5.8 - 7.2; Kinetics; Further Variations:; Reagents; |
2',3'-O-(isopropylidene)-5'-O-(triphenylmethyl)uridine
uridine
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 1.5h; detritylation; deketalization; | 98% |
Conditions | Yield |
---|---|
With purine nucleoside phosphorylase; thymidine phosphorylase; phosphoric acid In aq. phosphate buffer at 37℃; for 24h; pH=6.8; Enzymatic reaction; |
Conditions | Yield |
---|---|
With uridine phosphorylase In water; water-d2 at 37℃; for 20h; pH=6.9; Enzymatic reaction; | 85 %Spectr. |
2',5'-bis-O-(tert-butyldimethylsilyl)uridine
uridine
Conditions | Yield |
---|---|
With cyclohexene; trimethyleneglycol In methanol for 6h; Heating; | 100% |
Multi-step reaction with 2 steps 1: 80 percent / cyclohexene / PdO / methanol / Heating 2: cyclohexene / PdO / methanol / Heating View Scheme |
2'-O-{[(triisopropylsilyl)oxy]methyl}uridine
uridine
Conditions | Yield |
---|---|
With tetra(tert-butyl)-ammonium fluoride In tetrahydrofuran at 25℃; for 0.0833333h; | |
With tetrabutyl ammonium fluoride In tetrahydrofuran for 5h; |
uridine
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran for 3h; | |
With tetrabutyl ammonium fluoride In tetrahydrofuran for 3h; |
A
G
B
1-(β-D-ribofuranosyl)-4-pyrimidinone
C
uridine
D
CYTIDINE
E
adenosine
Conditions | Yield |
---|---|
Stage #1: 5'-CGGCUXUUAACCGA-3', X=2-deoxouridine With 1U P1 nuclease In aq. buffer at 37℃; for 16h; pH=7; Enzymatic reaction; Stage #2: With 2U alkaline phosphatase In aq. buffer at 37℃; for 1h; Enzymatic reaction; |
uridine
Conditions | Yield |
---|---|
With hexaaquaruthenium(II) tosylate In water at 40℃; for 36h; | 100% |
N3-<(methoxyethoxy)methyl>uridine
uridine
Conditions | Yield |
---|---|
With trityl tetrafluoroborate In water; acetonitrile for 1h; Ambient temperature; | 95% |
With pyridine; ammonium hydroxide at 50℃; for 5h; | 94% |
Conditions | Yield |
---|---|
Stage #1: sodium 7‐azido‐1,1‐difluoroheptane‐1‐sulfinate; Oceanobacillus iheyensis group II intron RNA pH=6.5; Stage #2: With tert.-butylhydroperoxide In water at 22℃; for 24h; Cooling with ice; Stage #3: Enzymatic reaction; |
phosphoric acid adenosin-3'-yl ester uridin-5'-yl ester
A
adenosine 2',3'-cyclic monophosphate
B
uridine
Conditions | Yield |
---|---|
With zinc(II) nitrate; sodium nitrate; HEPES buffer In water at 90.1℃; Rate constant; | |
With (Zn(2+))2*1,4-bis[(1,5,9-triazacyclododecan-3-yloxy)Me]C6H4 In various solvent(s) at 90℃; pH=5.8 - 7.2; Kinetics; Further Variations:; Reagents; | |
With zinc(II) nitrate; N2,N4-bis{2-[1,4,7,10-tetraazacyclododecan-1-yl]ethyl}-N6-{3-[1,5,9-triazacyclododecan-3-yl]propyl}-1,3,5-triazine-2,4,6-triamine; water In aq. buffer at 90℃; pH=6.84; Kinetics; |
Conditions | Yield |
---|---|
With dmap | 100% |
With triethylamine In 1,4-dioxane at 25℃; for 36h; | 100% |
With pyridine at 20℃; for 16h; | 100% |
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 1h; | 100% |
Stage #1: acetone; uridine With sulfuric acid at 20℃; for 1h; Stage #2: With triethylamine In acetone Product distribution / selectivity; | 100% |
With sulfuric acid at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetone for 1h; Reflux; | 100% |
With toluene-4-sulfonic acid In acetone for 1h; Reflux; | 99% |
With toluene-4-sulfonic acid In acetone at 60℃; for 24h; Inert atmosphere; | 96% |
tert-butylchlorodiphenylsilane
uridine
1-(5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)uracil
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 18h; Inert atmosphere; | 100% |
In pyridine for 48h; Ambient temperature; | 76% |
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; | 75.4% |
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
uridine
3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine
Conditions | Yield |
---|---|
With pyridine at 20℃; for 16h; Cooling with ice; | 100% |
With pyridine at 20℃; for 16h; Cooling with ice; | 100% |
With pyridine at 20℃; for 16h; | 100% |
Conditions | Yield |
---|---|
With iodine; silver nitrate In methanol at 20 - 40℃; | 100% |
With iodine; silver sulfate In methanol for 0.2h; Ambient temperature; | 93% |
With sodium azide; Iodine monochloride In acetonitrile at 25℃; for 24h; | 93% |
Conditions | Yield |
---|---|
With chloro-diisopropyl-amine In N,N-dimethyl-formamide at 20℃; Substitution; | 100% |
uridine
[5,6-2H2]-uridine
Conditions | Yield |
---|---|
With hydrogen; water-d2; palladium on activated charcoal at 160℃; for 24h; | 100% |
With water-d2; palladium on activated charcoal; hydrogen at 160℃; for 24h; | 100% |
uridine
1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; benzoic acid anhydride In N,N-dimethyl-formamide at 100℃; for 4h; | 100% |
With bis(phenyl) carbonate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 80 - 110℃; for 3h; | 95% |
With bis(phenyl) carbonate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 100 - 137℃; | 78% |
Conditions | Yield |
---|---|
With pyridine; dmap In acetonitrile for 0.25h; | 100% |
uridine
Conditions | Yield |
---|---|
With nitrogen; water-d2; potassium carbonate at 95℃; for 16h; Sealed tube; Inert atmosphere; | 100% |
With water-d2; potassium carbonate at 95℃; for 16h; Inert atmosphere; Sealed tube; | 100% |
With water-d2; potassium carbonate at 95℃; for 16h; Sealed tube; Inert atmosphere; | 100% |
With water-d2; triethylamine at 70℃; for 288h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: bis(phenyl) carbonate; uridine In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate at 115℃; for 4h; | 100% |
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; |
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 6.17h; silylation; | 99.6% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 11h; | 99% |
Conditions | Yield |
---|---|
bismuth(lll) trifluoromethanesulfonate In dichloromethane at 25℃; for 23h; Acylation; | 99% |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 25h; | 99% |
chlorodimethyl(1,1,2-trimethylpropyl)silane
uridine
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 18h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With hydrogen; rhodium contaminated with carbon In water for 24h; | 98% |
With hydrogen; palladium on activated charcoal In methanol under 2068.65 Torr; for 24h; | 96% |
With Rh/Al2O3; water Hydrogenation; |
tert-butyldimethylsilyl chloride
uridine
5'-O-(tert-butyldimethylsilyl)uridine
Conditions | Yield |
---|---|
With silver nitrate In tetrahydrofuran for 3h; Ambient temperature; add of (n-Bu)4NSO3H; | 98% |
With silver nitrate In tetrahydrofuran at 20℃; for 10h; | 98% |
silver nitrate In tetrahydrofuran for 1h; | 98% |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 1h; | 98% |
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 30℃; for 8h; regioselective reaction; | 96% |
With pyridine; silver nitrate In tetrahydrofuran for 1h; Ambient temperature; | 90% |
Conditions | Yield |
---|---|
In pyridine; dimethyl sulfoxide for 24h; Ambient temperature; | 98% |
With triethylamine for 0.025h; Microwave irradiation; neat (no solvent); | 75% |
With pyridine for 20h; | 71% |
In pyridine at 0 - 20℃; Inert atmosphere; |
Reported in EPA TSCA Inventory.
The Uridine, with the CAS registry number 58-96-8 and EINECS registry number 200-407-5, has the IUPAC name of 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione. It is a kind of white to slightly off-white powder, and belongs to the following product categories: Pyridines, Pyrimidines, Purines and Pteredines; Chiral; Biochemistry; Nucleosides and their analogs; Nucleosides, Nucleotides & Related Reagents; Nucleic acids. The molecular formula of the chemical is C9H12N2O6. What's more, it is a major material of some drugs, such as S-FC, IDUR, BDUR, etc. And it can be prepared by 2,4 - dichloro-(trimethylsiloxy) pyrimidine.
The Uridine is one of the four basic components of RNA, and plays a role in the glycolysis pathway of galactose. There is no catabolic process to metabolize galactose. Therefore, galactose is converted to glucose and metabolized in the common glucose pathway.
The physical properties of Uridine are as followings: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 3.288; (5)ACD/KOC (pH 7.4): 3.248; (6)#H bond acceptors: 8; (7)#H bond donors: 4; (8)#Freely Rotating Bonds: 5; (9)Polar Surface Area: 119.33 Å2; (10)Index of Refraction: 1.643; (11)Molar Refractivity: 52.732 cm3; (12)Molar Volume: 145.792 cm3; (13)Polarizability: 20.904×10-24cm3; (14)Surface Tension: 88.509 dyne/cm; (15)Density: 1.675 g/cm3.
You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Do not breathe dust and avoid contacting with skin and eyes; Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: c1cn(c(=O)[nH]c1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
(2)InChI: InChI=1/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1
(3)InChIKey: DRTQHJPVMGBUCF-XVFCMESIBG
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 4335mg/kg (4335mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Journal of Pharmacology and Experimental Therapeutics. Vol. 207, Pg. 504, 1978. |
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