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CAS 58-96-8 Uridine price
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58-96-8 Usage

Chemical Properties

White powder; odorless; slightly acrid and faintly sweet taste. Soluble in water; slightly soluble in dilute alcohol; insoluble in strong alcohol.

Applications

Uridine is phosphorylated to nucleotides, which are used for DNA and RNA synthesis as well as for the synthesis of membrane constituents and glycosylation[6-8]. Uridine plays a very important role in the glycolysis pathway of galactose. It can be used as a precursor in the production of CDP-choline. It is an important nutrient and widely used as a dietary supplement. It can improve the brain cholinergic functions and hepatic mitochondrial function in certain liver toxins. It plays a major role in pain physiology and brain energy utilization to maintain ATP production under restricted oxygen conditions[6, 8]. Uridine has many biological effects and, is thus can be used for the treatment of various kinds of diseases. In general, uridine can be used for the treatment for the following diseases such as cardiovascular disease and hypertension, respiratory dysfunction, liver disease, infertility, epilepsy, cancer & AIDS, Parkinsonism, anxiety, sleep dysfunction and Ischemia and hypoxia[7,8]. Effect on the central nerve system Uridine plays a crucial role in the pyrimidine metabolism of the brain. It supplies nervous tissue with the pyrimidine ring, and in turn, participates in a number of important metabolic pathways. Uridine and its nucleotide derivatives may also have an additional role in the function of the central nervous system as signaling molecules. Uridine administration had sleep-promoting and anti-epileptic actions, improved memory function and affected neuronal plasticity. Uridine can exert various kinds of effects on the central nerve system[CNS][1, 8-10]?It was found to be an active component of sleep-promoting substances in our brain[11, 12, 2] Anti-epileptogenic and anti-convulsant effect[3, 9, 10] Thermoregulatory effect[4, 13] long-term exposure to uridine improve our memory[5, 14] involved in the regulation of neuronal plasticity through for example that it enhances neurite outgrowth[15]. Based on those above findings, it can be used for the treatment of various diseases such as developmental delay, seizures, ataxia, severe language deficit, age-related cognitive decline and even Alzheimer's disease and Parkinson's disease. Uridine might also be useful as a nutrition supplement during development. Uridine[as uridine monophosphate] is found in mother's milk and has been proposed to play a role in regulatory mechanism through which plasma composition influences brain development[16]. Cystic fibrosis Cystic fibrosis is characterized by abnormal fluid transport across many epithelia including airways, pancreas, sweat glands and small intestine. This disease is associated with decreased Cl2 transport and increased Na+ transport. The disease is caused by an absence or dysfunction of the cystic fibrosis transmembrane conductance regulator[CFTR], a Clchannel expressed by epithelial cells, and by an increase in active Na+ absorption[17, 18]. The uridine nucleotide can be used for the treatment of cystic fibrosis since UTP activates P2 purinoceptors, bypasses the defective Clsecretion to activate an alternative Ca2+ -dependent Clsecretory pathway, further stimulating Clsecretion in epithelial cells and decreased Na+ absorption[18]. Effects on the circulatory system The effects of uridine and its nucleotides on isolated blood vessels are complex, sometimes acting directly on smooth muscle cells, at other times stimulating surrounding endothelial cells. Uridine and its nucleotides produce opposing effects in some tissues, which suggests that these ligands could act at distinct receptors or via intracellular messenger systems. Further studies are warranted, because many of these effects were observed at potentially physiological levels, and could aid the development of a novel series of antihypertensive agents based on uridine analogues[19]. Modulation of reproduction An important function of uridine could be to promote sperm motility, as seminal plasma uridine concentrations are positively correlated to percentage sperm motility[20]. It is perhaps relevant, therefore, that regulation of uridine diphosphatase during spermatogenesis in the rat was reported to be under hormonal control. The predominance of uridine in seminal fluids must lead to questions about its role in the environment of fertilization and implantation, but as yet these remain unanswered[21]. Cancer and antiviral therapy Uridine and UDP?glucose have been used to counter the unwanted toxicity of pyrimidine-based anticancer drugs. Uridine has been used as a rescue therapy for myelotoxicity and gastrointestinal toxicity produced by 5-fluorouracil[22]. Uridine and benzylacyclouridine protected mice against the neurotoxic side effects of pyrimidine-based drugs, such as azidothymidine used to treat HIV infection[23].

Biosynthesis and source

Uridine is widely produced in the form of uridine monophosphate[uridylate] through the decarboxylation of orotidylate, being catalyzed by orotidylate decarboxylase[4]. The orotidylate is produced from orotate, which is combined with 5-phosphoribosyl-1-pyrophosphate[PRPP] to form orotidylate by pyrimidine phosphoribosyltransferase. PRPP is created from ribose-5-phosphate by a further phosphorylation, serving as an energetic molecule to drive the reaction forward, while orotate is generated in several steps from carbamoyl phosphate and aspartate[4]. Diet is not an important source of uridine. Clinical studies and animal experimentation suggest that the liver synthesizes and degrades uridine, and is likely to have a central role in maintaining plasma uridine. Blood platelets and storage organelles of various species are reported to contain UTP and may provide releasable pools of uridine after catabolism[5].

Reference

www.cell.com/trends/pharmacological-sciences/pdf/S0165-6147(99]01298-5.pdf https://www.trc-canada.com/product-detail/?CatNum=U829919&CAS=&Chemical_Name=Uridine[1’-D]&Mol_Formula=C?DH??N?O? www.technologynetworks.com/genomics/lists/what-are-the-key-differences-between-dna-and-rna-296719 Berg JM, Tymoczko JL, Stryer L.[2002]. "Section 25.1In de Novo Synthesis, the Pyrimidine Ring Is Assembled from Bicarbonate, Aspartate, and Glutamine". Biochemistry[5th ed.]. W H Freeman. Goetz, U, P. M. Da, and A. Pletscher. "Adenine-, guanineand uridine-5'-phosphonucleotides in blood platelets and storage organelles of various species. " Journal of Pharmacology & Experimental Therapeutics178.1(1971]:210-215. L Ipata, P.; Pesi, R. Metabolic Regulation of Uridine in the Brain. Curr Metabolomics 2015, 3[1], 4-9. Connolly, G. P., and J. A. Duley. "Uridine and its nucleotides: biological actions, therapeutic potentials. " Trends in Pharmacological Sciences20.5(1999]:218-25. Dobolyi, and Arpad. Uridine Function in the Central Nervous System. Law, politics and the judicial system in Canada /. University of Calgary Press, 2011:743-751. Yegutkin, G. G. Nucleotideand nucleoside-converting coenzymes: Important modulators of purinergic signalling cascade. Biochim. Biophys. Acta-Mol. Cell. Res., 2008, 1783, 673-694.? Burnstock, G. Physiology and pathophysiology of purinergic neurotransmission. Physiol. Rev., 2007, 87, 659-797.? Borbely, A. A.; Tobler, I. Endogenous sleep-promoting substances and sleep regulation. Physiol. Rev., 1989, 69, 605-670.? Inoue, S. Sleep and sleep substances. Brain Dev., 1986, 8, 469-473.? Peters, G. J.; van Groeningen, C. J.; Laurensse, E. J.; Lankelma, J.; Leyva, A.; Pinedo, H. M. Uridine-induced hypothermia in mice and rats in relation to plasma and tissue levels of uridine and its metabolites. Cancer Chemother. Pharmacol., 1987, 20, 101-108.? Teather, L. A.; Wurtman, R. J. Chronic administration of UMP ameliorates the impairment of hippocampal-dependent memory in impoverished rats. J. Nutr., 2006, 136, 2834-2837.? Pooler, A. M.; Guez, D. H.; Benedictus, R.; Wurtman, R. J. Uridine enhances neurite outgrowth in nerve growth factor-differentiated PC12 [corrected]. Neuroscience, 2005, 134, 207-214.? Wurtman, R. J. Synapse formation and cognitive brain development: effect of docosahexaenoic acid and other dietary constituents. Metabol. Clin. Exp., 2008, 57, S6-S10.? Knowles, Michael R, L. L. Clarke, and R. C. Boucher. "Activation by Extracellular Nucleotides of Chloride Secretion in the Airway Epithelia of Patients with Cystic Fibrosis." N Engl J Med 325.8(1991]:533-538. Bennett, W D, et al. "Effect of uridine 5'-triphosphate plus amiloride on mucociliary clearance in adult cystic fibrosis. " American Journal of Respiratory & Critical Care Medicine 153.6 Pt 1(1996]:1796. Seifert, R, and G. Schultz. "Involvement of pyrimidinoceptors in the regulation of cell functions by uridine and by uracil nucleotides. " Trends in Pharmacological Sciences 10.9(1989]:365-369. Ronquist, G., B. Stegmayr, and F. Niklasson. "Sperm Motility and Interactions Among Seminal Uridine, Xanthine, Urate, and Atpase in Fertile and Infertile Men." Archives of Andrology 15.1(1985]:21-27. Xuma, M, and R. W. Turkington. "Hormonal regulation of uridine diphosphatase during spermatogenesis in the rat." Endocrinology91.2(1972]:415. Leyva, A, et al. "Phase I and pharmacokinetic studies of high-dose uridine intended for rescue from 5-fluorouracil toxicity. " Cancer Research 44.12 Pt 1(1984]:5928-5933. Calabresi, P, et al. "Benzylacyclouridine reverses azidothymidine-induced marrow suppression without impairment of anti-human immunodeficiency virus activity." Blood 76.11(1990]:2210-5.

Definition

The nucleoside formed when uracil is linked to D-ribose by a β-glycosidic bond.

Uses

Uridine is a nucleoside, contains a uracil attached to a ribose ring via a β-N1-glycosidic bond

Uses

Uridine is a nucleoside; widely distributed in nature. Uridine is one of the four basic components of ribonucleic acid (RNA)

Overview

Uridine is one of the key nucleotide that making RNA[1-3]. It is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring[or more specifically, a ribofuranose] via a β-N1-glycosidic bond. It is one of the five standard nucleosides which make up nucleic acids[including both RNA and DNA] with the others four being adenosine, thymidine, cytidine and guanosine. The five nucleosides are commonly abbreviated to their one-letter codes U, A, T, C and G respectively. Thymidine is found in deoxyribonucleic acid[DNA] and not ribonucleic acid(RNA]. Conversely, uridine is found in RNA and not DNA[1, 3]. The remaining three nucleosides can be found in both RNA and DNA. In RNA, they would be represented as A, C and G whereas in DNA they would be represented as dA, dC and dG[1,3].

Definition

A nucleoside consistingof one uracil molecule linked to a dribosesugar molecule. The derivedmucleotide uridine diphosphate(UDP) is important in carbohydratemetabolism.

Uses

A nucleoside and one of main component in RNA.

Purification Methods

Crystallise -uridine from aqueous 75% MeOH or EtOH (m 165-166o). [Beilstein 24 III/IV 1202.]
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-/m0/s1

58-96-8 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (U0020)  Uridine  >98.0%(HPLC)(T) 58-96-8 5g 290.00CNY Detail
TCI America (U0020)  Uridine  >98.0%(HPLC)(T) 58-96-8 25g 730.00CNY Detail
Alfa Aesar (A15227)  Uridine, 99%    58-96-8 5g 266.0CNY Detail
Alfa Aesar (A15227)  Uridine, 99%    58-96-8 25g 947.0CNY Detail
Alfa Aesar (A15227)  Uridine, 99%    58-96-8 100g 3178.0CNY Detail
USP (1707114)  Uridine  United States Pharmacopeia (USP) Reference Standard 58-96-8 1707114-15MG 4,647.24CNY Detail

58-96-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name uridine

1.2 Other means of identification

Product number -
Other names NFDB2

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58-96-8 SDS

58-96-8Synthetic route

5'-O-trityluridine
6554-10-5

5'-O-trityluridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
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%
tribenzoyl uridine
1748-04-5

tribenzoyl uridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
With methanol; ammonia at 20℃;91%
With methanol; sodium methylate at 20℃; for 2h;87%
With triethylamine In methanol; water83%
With sodium methylate In methanol Ambient temperature;
2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine
64898-15-3

2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
With SO3H silica gel In ethyl acetate at 20℃; for 15h;81%
CYTIDINE
65-46-3

CYTIDINE

uridine
58-96-8

uridine

Conditions
ConditionsYield
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;
2',3'-O-isopropylideneuridine
362-43-6

2',3'-O-isopropylideneuridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
69304-38-7

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
Reaxys ID: 11351538

Reaxys ID: 11351538

uridine
58-96-8

uridine

Conditions
ConditionsYield
With Levalit MDS 1368 cation exchanger (Na-form) In water at 80℃;49%
Tri-O-acetyluridine
4105-38-8

Tri-O-acetyluridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
81246-79-9

5'-dimethoxytrityluridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
133766-24-2

2'-O-allyluridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
51600-12-5

5'-O-monomethoxytrityluridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
C13H16N3O9(1-)*Na(1+)

C13H16N3O9(1-)*Na(1+)

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
820212-19-9

2′,3′-O-bis-(benzyloxycarbonyl)uridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
With cyclohexa-1,4-diene; palladium on activated charcoal In N,N-dimethyl-formamide for 1.5h;99%
uracil
66-22-8

uracil

adenosine
58-61-7

adenosine

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
54925-67-6

3',5'-bis-O-(tert-butyldimethylsilyl)uridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
C18H21N3O10

C18H21N3O10

uridine
58-96-8

uridine

Conditions
ConditionsYield
With ammonium chloride; zinc In methanol at 20℃; for 2h;
C19H23N3O11

C19H23N3O11

uridine
58-96-8

uridine

Conditions
ConditionsYield
With ammonium chloride; zinc In methanol at 20℃;
3-methyluridine
2140-69-4

3-methyluridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Irradiation; chemoselective reaction;98%
uridylyl-3',5'-uridine
2415-43-2

uridylyl-3',5'-uridine

A

uridine 2',3'-cyclic phosphate
606-02-0

uridine 2',3'-cyclic phosphate

B

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
10526-27-9

2',3'-O-(isopropylidene)-5'-O-(triphenylmethyl)uridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 1.5h; detritylation; deketalization;98%
uracil
66-22-8

uracil

Inosine
58-63-9

Inosine

uridine
58-96-8

uridine

Conditions
ConditionsYield
With purine nucleoside phosphorylase; thymidine phosphorylase; phosphoric acid In aq. phosphate buffer at 37℃; for 24h; pH=6.8; Enzymatic reaction;
α-D-ribofuranose-1-O-phosphate disodium salt

α-D-ribofuranose-1-O-phosphate disodium salt

uracil
66-22-8

uracil

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
54925-66-5

2',5'-bis-O-(tert-butyldimethylsilyl)uridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
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
468757-56-4

2'-O-{[(triisopropylsilyl)oxy]methyl}uridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
With tetra(tert-butyl)-ammonium fluoride In tetrahydrofuran at 25℃; for 0.0833333h;
With tetrabutyl ammonium fluoride In tetrahydrofuran for 5h;
3‘,5’-O-(tetraisopropyldisilane-1,2-diyl)uridine

3‘,5’-O-(tetraisopropyldisilane-1,2-diyl)uridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 3h;
With tetrabutyl ammonium fluoride In tetrahydrofuran for 3h;
5'-CGGCUXUUAACCGA-3', X=2-deoxouridine

5'-CGGCUXUUAACCGA-3', X=2-deoxouridine

B

1-(β-D-ribofuranosyl)-4-pyrimidinone
21052-20-0

1-(β-D-ribofuranosyl)-4-pyrimidinone

C

uridine
58-96-8

uridine

D

CYTIDINE
65-46-3

CYTIDINE

E

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
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;
5'-O-allyluridine

5'-O-allyluridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
With hexaaquaruthenium(II) tosylate In water at 40℃; for 36h;100%
N3-<(methoxyethoxy)methyl>uridine
89257-63-6

N3-<(methoxyethoxy)methyl>uridine

uridine
58-96-8

uridine

Conditions
ConditionsYield
With trityl tetrafluoroborate In water; acetonitrile for 1h; Ambient temperature;95%
With pyridine; ammonium hydroxide at 50℃; for 5h;94%
sodium 7‐azido‐1,1‐difluoroheptane‐1‐sulfinate

sodium 7‐azido‐1,1‐difluoroheptane‐1‐sulfinate

Oceanobacillus iheyensis group II intron RNA

Oceanobacillus iheyensis group II intron RNA

A

C17H24F2N8O5

C17H24F2N8O5

C

uridine
58-96-8

uridine

D

CYTIDINE
65-46-3

CYTIDINE

E

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
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
3051-84-1

phosphoric acid adenosin-3'-yl ester uridin-5'-yl ester

A

adenosine 2',3'-cyclic monophosphate
634-01-5

adenosine 2',3'-cyclic monophosphate

B

uridine
58-96-8

uridine

Conditions
ConditionsYield
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;
acetic anhydride
108-24-7

acetic anhydride

uridine
58-96-8

uridine

Tri-O-acetyluridine
4105-38-8

Tri-O-acetyluridine

Conditions
ConditionsYield
With dmap100%
With triethylamine In 1,4-dioxane at 25℃; for 36h;100%
With pyridine at 20℃; for 16h;100%
acetone
67-64-1

acetone

uridine
58-96-8

uridine

2',3'-O-isopropylideneuridine
362-43-6

2',3'-O-isopropylideneuridine

Conditions
ConditionsYield
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%
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

uridine
58-96-8

uridine

2',3'-O-isopropylideneuridine
362-43-6

2',3'-O-isopropylideneuridine

Conditions
ConditionsYield
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
58479-61-1

tert-butylchlorodiphenylsilane

uridine
58-96-8

uridine

1-(5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)uracil
130351-68-7

1-(5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)uracil

Conditions
ConditionsYield
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
69304-37-6

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

uridine
58-96-8

uridine

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine
69304-38-7

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Conditions
ConditionsYield
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%
uridine
58-96-8

uridine

5-iodouridine
1024-99-3

5-iodouridine

Conditions
ConditionsYield
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%
triphenylphosphine
603-35-0

triphenylphosphine

uridine
58-96-8

uridine

2',3'-O-Triphenylphosphoranediyluridine

2',3'-O-Triphenylphosphoranediyluridine

Conditions
ConditionsYield
With chloro-diisopropyl-amine In N,N-dimethyl-formamide at 20℃; Substitution;100%
uridine
58-96-8

uridine

[5,6-2H2]-uridine
40632-21-1

[5,6-2H2]-uridine

Conditions
ConditionsYield
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
58-96-8

uridine

1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one
847650-91-3

1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one

Conditions
ConditionsYield
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%
pivaloyl chloride
3282-30-2

pivaloyl chloride

uridine
58-96-8

uridine

C29H44N2O10
1228354-92-4

C29H44N2O10

Conditions
ConditionsYield
With pyridine; dmap In acetonitrile for 0.25h;100%
uridine
58-96-8

uridine

[5-(2)H]-uridine

[5-(2)H]-uridine

Conditions
ConditionsYield
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%
bis(phenyl) carbonate
102-09-0

bis(phenyl) carbonate

uridine
58-96-8

uridine

2,2'-Anhydrouridine
3736-77-4

2,2'-Anhydrouridine

Conditions
ConditionsYield
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;
triethylsilyl chloride
994-30-9

triethylsilyl chloride

uridine
58-96-8

uridine

2',3',5'-tris-O-(triethylsilyl)uridine
190836-61-4

2',3',5'-tris-O-(triethylsilyl)uridine

Conditions
ConditionsYield
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%
2,2-dimethylpropanoic anhydride
1538-75-6

2,2-dimethylpropanoic anhydride

uridine
58-96-8

uridine

2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-(2,2-dimethyl-propionyloxy)-5-(2,2-dimethyl-propionyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-(2,2-dimethyl-propionyloxy)-5-(2,2-dimethyl-propionyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Conditions
ConditionsYield
bismuth(lll) trifluoromethanesulfonate In dichloromethane at 25℃; for 23h; Acylation;99%
butanoic acid anhydride
106-31-0

butanoic acid anhydride

uridine
58-96-8

uridine

2',3',4'-tri-O-butyryluridine

2',3',4'-tri-O-butyryluridine

Conditions
ConditionsYield
With pyridine at 20℃; for 25h;99%
chlorodimethyl(1,1,2-trimethylpropyl)silane
67373-56-2

chlorodimethyl(1,1,2-trimethylpropyl)silane

uridine
58-96-8

uridine

5'-O-(dimethylthexylsilyl)uridine

5'-O-(dimethylthexylsilyl)uridine

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 18h; Inert atmosphere;99%
uridine
58-96-8

uridine

5,6-dihydrouridine
5627-05-4

5,6-dihydrouridine

Conditions
ConditionsYield
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
18162-48-6

tert-butyldimethylsilyl chloride

uridine
58-96-8

uridine

5'-O-(tert-butyldimethylsilyl)uridine
87418-77-7, 54925-65-4

5'-O-(tert-butyldimethylsilyl)uridine

Conditions
ConditionsYield
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%
4,4'-dimethoxytrityl chloride
40615-36-9

4,4'-dimethoxytrityl chloride

uridine
58-96-8

uridine

5'-dimethoxytrityluridine
81246-79-9

5'-dimethoxytrityluridine

Conditions
ConditionsYield
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%
uridine
58-96-8

uridine

mono-4-methoxytrityl chloride
14470-28-1

mono-4-methoxytrityl chloride

5'-O-monomethoxytrityluridine
51600-12-5

5'-O-monomethoxytrityluridine

Conditions
ConditionsYield
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;

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