O5'-trityl-2'-deoxy-uridine
2'-deoxyuridine
Conditions | Yield |
---|---|
With silica gel; trifluoroacetic acid In methanol; chloroform | 100% |
Conditions | Yield |
---|---|
With cytidine deaminase enzyme In aq. phosphate buffer at 37℃; for 0.0833333h; pH=7; Enzymatic reaction; | 99% |
With acetic acid; sodium nitrite | |
With sodium hydroxide at 90.1℃; Rate constant; Mechanism; various reagent concentration, decomposition to nonchromophoric products; |
4-O-(2,4,6-Trimethylphenyl)-2'-deoxyuridine
A
2'-deoxyuridine
B
2'-Deoxycytidine
Conditions | Yield |
---|---|
With ammonium hydroxide at 65℃; for 2h; | A n/a B 98% |
Conditions | Yield |
---|---|
With triethylamine In methanol; water at 4℃; for 12h; Irradiation; sensitizer: methylene blue; | 96% |
Multi-step reaction with 3 steps 1: 99.7 percent / p-toluenesulfonic acid / tetrahydrofuran / 2 h / Ambient temperature 2: n-BuLi, MeI / tetrahydrofuran; hexane / -78 °C 3: 1N HCl / methanol / 0.08 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: (NH4)2SO4 / Heating 2: 1) PdCl3, Ph3P, 2) NH4Cl, H2O / 1) THF, reflux, 12 h, 2) MeOH, reflux, 3 h View Scheme | |
With sodium tetrahydroborate; Naphthalene-1,8-diselenol In aq. phosphate buffer at 37℃; pH=7; Reagent/catalyst; | |
With sodium tetrahydroborate; C10H8Te In aq. phosphate buffer at 37℃; pH=7; Kinetics; Reagent/catalyst; |
3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine
2'-deoxyuridine
Conditions | Yield |
---|---|
With K 10 clay In methanol; water at 75℃; for 12h; | 94% |
3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine
2'-deoxyuridine
Conditions | Yield |
---|---|
With K 10 clay In methanol; water at 75℃; for 60h; | 90% |
With tetrabutyl ammonium fluoride Yield given; |
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; Escherichia coli thymidine phosphorylase; Escherichia coli purine nucleoside phosphorylase In aq. buffer at 20℃; for 20h; pH=7.5; Enzymatic reaction; | 80% |
dibutyl disulfide
C5-chloromercuri-2'-deoxyuridine
A
2'-deoxyuridine
B
5-(1-Thiapentyl)-2'-deoxyuridine
Conditions | Yield |
---|---|
With lithium tetrachloropalladate(II) In methanol for 16h; Ambient temperature; | A n/a B 73% |
With lithium tetrachloropalladate(II) In methanol for 16h; Ambient temperature; other organic disulfides; | A n/a B 73% |
3'-O-acetyl-5'-O-t-butyldimethylsilyl-2'-deoxyuridine
benzyl alcohol
A
(benzyloxy)(tert-butyl)dimethylsilane
B
2'-deoxyuridine
C
uracil
D
3'-O-acetyl-2'-deoxyuridine
Conditions | Yield |
---|---|
With copper(II) sulfate In xylene for 2h; Heating; | A n/a B n/a C n/a D 72% |
Conditions | Yield |
---|---|
Multistep reaction; | 60% |
Multi-step reaction with 4 steps 1: 90 percent / pyridine / 2 h / Ambient temperature 2: 4-(dimethylamino)pyridine / acetonitrile / 6 h / Ambient temperature 3: tri-n-butylstannane, α,α'-azoisobutyronitrile / toluene / 3 h / 75 °C 4: tetra-n-butylammonium fluoride View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide; bis(phenyl) carbonate / N,N-dimethyl-formamide / 12 h / 140 °C 2: hydrogenchloride / N,N-dimethyl-formamide / 14 h / 40 °C 3: sodium hydroxide; nickel; hydrogen / methanol / 20 h / 40 °C View Scheme |
3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine
benzyl alcohol
A
(benzyloxy)(tert-butyl)dimethylsilane
B
2'-deoxyuridine
C
thymin
Conditions | Yield |
---|---|
With copper(II) sulfate In xylene Heating; | A 0.92 g B 53% C n/a |
C5-chloromercuri-2'-deoxyuridine
diphenyldisulfane
A
2'-deoxyuridine
B
5-phenylsulfanyl-2'-deoxyuridine
Conditions | Yield |
---|---|
With lithium tetrachloropalladate(II) In methanol for 16h; Ambient temperature; | A n/a B 52% |
C5-chloromercuri-2'-deoxyuridine
N,N'-Bis(trifluoroacetyl)cystamine
A
2'-deoxyuridine
B
5-<3-(Trifluoroacetamido)-1-thiapropyl>-2'-deoxyuridine
Conditions | Yield |
---|---|
With lithium tetrachloropalladate(II) In methanol for 16h; Ambient temperature; | A n/a B 51% |
5-Iodo-2'-deoxyuridine
allyl-trimethyl-silane
A
2'-deoxyuridine
B
C5-(allyl)-2'-deoxyuridine
Conditions | Yield |
---|---|
In water; acetonitrile Irradiation; | A 31% B 49% |
In water; acetonitrile for 10h; Ambient temperature; Irradiation; | A 31% B 49% |
Conditions | Yield |
---|---|
With allyl-trimethyl-silane In water; acetonitrile Irradiation; | A 31% B 49% |
With allyl-trimethyl-silane In water; acetonitrile for 10h; Ambient temperature; Irradiation; | A 31% B 49% |
2'-deoxy-3',5'-bis-O-triphenylmethyluridine
benzyl alcohol
A
triphenylmethane
B
benzyl trityl ether
C
2'-deoxyuridine
D
uracil
Conditions | Yield |
---|---|
With copper(II) sulfate In xylene for 5h; Heating; | A n/a B n/a C 49% D n/a |
1-((2R,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
benzyl alcohol
A
(benzyloxy)(tert-butyl)dimethylsilane
B
2'-deoxyuridine
C
thymin
Conditions | Yield |
---|---|
With copper(II) sulfate In xylene Heating; | A n/a B 49% C n/a |
O5'-trityl-2'-deoxy-uridine
benzyl alcohol
A
triphenylmethane
B
benzyl trityl ether
C
2'-deoxyuridine
D
uracil
Conditions | Yield |
---|---|
With copper(II) sulfate In xylene for 5h; Heating; | A n/a B n/a C 49% D n/a |
dimethyl 3,3'-dithiodipropionate
C5-chloromercuri-2'-deoxyuridine
A
2'-deoxyuridine
B
5-<3-(Methoxycarbonyl)-1-thiapropyl>-2'-deoxyuridine
Conditions | Yield |
---|---|
With lithium tetrachloropalladate(II) In methanol for 16h; Ambient temperature; | A n/a B 46% |
morpholine
cyclohexa-1,4-diene
5-Iodo-2'-deoxyuridine
B
2'-deoxyuridine
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; zinc(II) chloride; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 100℃; for 24h; | A n/a B 40% |
O5'-trityl-2'-deoxy-uridine
A
2'-deoxy-3'-O-triphenylmethyluridine
B
2'-deoxy-3',5'-bis-O-triphenylmethyluridine
C
2'-deoxyuridine
D
uracil
Conditions | Yield |
---|---|
With copper(II) sulfate In xylene for 4h; Heating; | A 6% B 37% C 10% D n/a |
1-((2R,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
A
2'-deoxyuridine
B
3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine
C
1-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
D
uracil
Conditions | Yield |
---|---|
With copper(II) sulfate In xylene Heating; | A 10% B 36% C 6% D n/a |
5-tert-Butyl-2'-deoxyuridine
A
2'-deoxyuridine
Conditions | Yield |
---|---|
In water for 48h; Irradiation; | A n/a B 35% |
Conditions | Yield |
---|---|
In various solvent(s) at 37℃; for 72h; pH=7.4; Kinetics; | A 11.1% B 13.4% C 28% |
O5'-acetyl-2'-iodo-2'-deoxy-uridine
2'-deoxyuridine
Conditions | Yield |
---|---|
With Pd-BaSO4; ammonia Hydrogenation; |
1-(O3,O5-bis-trimethylsilanyl-β-D-erythro-2-deoxy-pentofuranosyl)-5-bromo-4-trimethylsilanyloxy-1H-pyrimidin-2-one
trimethylaluminum
A
2'-deoxyuridine
B
thymidine
Conditions | Yield |
---|---|
With water; ammonium chloride; triphenylphosphine 1) THF, reflux, 12 h, 2) MeOH, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given; |
chloro-trimethyl-silane
perfluoropropylene
5-Iodo-2'-deoxyuridine
A
2'-deoxyuridine
B
(E)-2'-deoxy-5-(perfluoropropen-1-yl)uridine
C
(Z)-2'-deoxy-5-(perfluoropropen-1-yl)uridine
D
5-Trimethylsilyl-2'-deoxy-β-uridine
Conditions | Yield |
---|---|
With pyridine; n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane Yield given. Multistep reaction. Title compound not separated from byproducts; |
chloro-trimethyl-silane
Chlorotrifluoroethylene
5-Iodo-2'-deoxyuridine
A
2'-deoxyuridine
B
(E)-5-(2-chloro-1,2-difluorovinyl)-2'-deoxyuridine
C
(Z)-5-(2-chloro-1,2-difluorovinyl)-2'-deoxyuridine
D
5-Trimethylsilyl-2'-deoxy-β-uridine
Conditions | Yield |
---|---|
With pyridine; n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane Yield given. Multistep reaction. Yields of byproduct given; | |
With pyridine; n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With hydrogen; Rh/Al2O3 In methanol under 1810.02 Torr; for 4h; | 100% |
With 5% Rh/Al2O3; hydrogen In water under 2327.23 Torr; for 18h; | 100% |
With Rh/Al2O3; hydrogen In water at 20℃; under 22502.3 Torr; | 96% |
Conditions | Yield |
---|---|
With iodine; silver nitrate In methanol at 40℃; for 3h; | 100% |
With iodine; silver nitrate In methanol at 40℃; for 3h; | 100% |
With sodium azide; Iodine monochloride In acetonitrile at 25℃; for 24h; Product distribution; Mechanism; other uracil nucleosides; other halogenation agents; var. temp. and time; | 96% |
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane
2'-deoxyuridine
3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 23h; | 100% |
With pyridine for 2h; | 94% |
With pyridine for 2.5h; Ambient temperature; | 91.5% |
Conditions | Yield |
---|---|
With dmap | 100% |
With pyridine at 20℃; for 24h; | 100% |
With pyridine at 0 - 20℃; for 5h; Acetylation; | 99% |
2'-deoxyuridine
tert-butyldimethylsilyl chloride
3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; for 3h; | 100% |
With pyridine; 1H-imidazole at 0 - 20℃; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide Etherification; | 97% |
2'-deoxyuridine
tert-butylchlorodiphenylsilane
1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at -50 - 20℃; for 4h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 1h; | 87% |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 17h; | 76% |
With dmap In pyridine | |
With pyridine at 20℃; Etherification; |
Conditions | Yield |
---|---|
With pyridine for 3h; Ambient temperature; | 99% |
In pyridine at 20℃; for 3h; | 98% |
With pyridine at 20℃; for 21h; | 93% |
2'-deoxyuridine
mono-4-methoxytrityl chloride
O5'-trityl-2'-deoxy-uridine
Conditions | Yield |
---|---|
With pyridine for 2h; Heating / reflux; | 99% |
2'-deoxyuridine
mono-4-methoxytrityl chloride
1-{4-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydrofuran-2-yl}-1H-pyrimidine-2,4-dione
Conditions | Yield |
---|---|
With pyridine for 2h; Heating; | 99% |
With pyridine; dmap at 50℃; for 40h; Inert atmosphere; | 69% |
Conditions | Yield |
---|---|
With 1-(2-methoxyethyl)-3-methylimidazolium trifluoroacetate; N-Bromosuccinimide at 25℃; for 0.0833333h; | 98% |
With N-Bromosuccinimide; sodium azide In 1,2-dimethoxyethane; water at 25℃; for 24h; | 90% |
With ammonium cerium (IV) nitrate; 1-ethylene glycol monomethyl ether-3-methylimidazolium methanesulfonate; lithium bromide at 80℃; for 0.333333h; | 86% |
2'-deoxyuridine
pivaloyl chloride
O5'-(2,2-dimethyl-propionyl)-2'-deoxy-uridine
Conditions | Yield |
---|---|
With pyridine at -20℃; for 3h; | 98% |
Conditions | Yield |
---|---|
With 18-crown-6 ether In dimethyl sulfoxide at 50℃; for 36h; | 97.3% |
With Lactobacillus animalis ATCC 35046 2’-N-deoxyribosyltransferase immobilized in DEAE-Sepharose; water for 1h; Enzymatic reaction; | 22% |
With potassium phosphate; 5'-amino-5'-deoxyuridine phosphorylase In Tris HCl buffer at 30℃; for 3h; pH=9; Kinetics; Concentration; Time; Enzymatic reaction; |
2'-deoxyuridine
di-tert-butylsilyl bis(trifluoromethanesulfonate)
1-[3,5-O-(di-tert-butylsilylene)-2-deoxy-β-D-ribofuranosyl]uracil
Conditions | Yield |
---|---|
97% | |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; | 91% |
Conditions | Yield |
---|---|
With pyridine at 50℃; | 97% |
With pyridine; dmap Inert atmosphere; Heating; | 93% |
With pyridine at 100℃; for 18h; | 12.58 g |
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; purine nucleoside phosphorylase Escherichia coli; uridine phosphorylase Escherichia coli In aq. phosphate buffer at 50℃; for 3h; pH=7.0; Kinetics; Enzymatic reaction; diastereoselective reaction; | 97% |
Conditions | Yield |
---|---|
With purine nucleoside phosphorylase; uridine phosphorylase In aq. phosphate buffer; dimethyl sulfoxide at 60℃; for 5h; pH=7; Solvent; Temperature; Enzymatic reaction; | 96% |
2'-deoxyuridine
benzoyl chloride
3',5'-Di-O-benzoyl-2'-deoxyuridine
Conditions | Yield |
---|---|
In pyridine at 0℃; for 1h; | 95% |
With pyridine at 50 - 55℃; for 72h; | 91% |
With pyridine for 1h; Ambient temperature; |
Conditions | Yield |
---|---|
at 37℃; for 7h; alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli, ammonium acetate buffer pH 5.8; | 95% |
Conditions | Yield |
---|---|
With copper diacetate In dimethyl sulfoxide at 60℃; for 16h; | 95% |
Conditions | Yield |
---|---|
With recombinant Escherichia coli purine nucleoside phosphorylase Ser90Ala mutant In aq. phosphate buffer; dimethyl sulfoxide at 50℃; for 24h; pH=7; Reagent/catalyst; Enzymatic reaction; | 95% |
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% |
para-chlorotoluene
2'-deoxyuridine
2'-deoxy-3',5'-di-O-(4-methylbenzoyl)uridine
Conditions | Yield |
---|---|
In pyridine 1.) 0 degC to R.T., 2.) 50 degC, 2 h; | 94% |
triethylsilyl chloride
2'-deoxyuridine
2'-deoxy-3',5'-bis-O-(triethylsilyl)uridine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 23℃; for 16h; | 94% |
Conditions | Yield |
---|---|
Stage #1: 2'-deoxyuridine With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In water at 80℃; for 0.0833333h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry; Stage #2: 2-benzofuranyl boronic acid With triethylamine In water at 80℃; Reagent/catalyst; Temperature; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry; | 94% |
Conditions | Yield |
---|---|
With uridine phosphorylase; purine nucleosidephosphorylase E.coli In aq. phosphate buffer at 50℃; for 2.5h; pH=7; Enzymatic reaction; | 93% |
The 2'-Deoxyuridine, with the CAS registry number 951-78-0 and EINECS registry number 213-455-7, has the IUPAC name of 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione. It is a kind of white crystalline powder which is also air sensitive. The molecular formula of the chemical is C9H12N2O5. What's more, while dealing with this chemical, you should not breathe dust and then try to avoid contacting with skin and eyes.
The physical properties of 2'-Deoxyuridine are as followings: (1)ACD/LogP: -1.70; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.7; (4)ACD/LogD (pH 7.4): -1.74; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.82; (8)ACD/KOC (pH 7.4): 2.58; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 68.31 Å2; (13)Index of Refraction: 1.603; (14)Molar Refractivity: 51.14 cm3; (15)Molar Volume: 148.8 cm3; (16)Polarizability: 20.27×10-24cm3; (17)Surface Tension: 71.1 dyne/cm; (18)Density: 1.533 g/cm3.
Uses of 2'-Deoxyuridine: It is always used as an uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease. And it is also used as intermediates.
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 gloves and eye/face protection, 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: O=C/1NC(=O)N(\C=C\1)C2O[C@@H]([C@@H](O)C2)CO
(2)InChI: InChI=1/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8?/m0/s1
(3)InChIKey: MXHRCPNRJAMMIM-FWHJPCMOBR
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