4105-38-8

Basic information

• Product Name: 2',3',5'-Tri-O-acetyluridine
• Synonyms: RG 2133;Tri-O-acetyl uridine;Uridine triacetate;Vistonuridine;1-((2R,3R,4R,5R)-3,4-Diacetyl-3,4-dihydroxy-5-(1-hydroxy-2-oxopropyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione;2',3',5'-Tri-O-acetyl-rU;(2R,3R,4R,5R)-2-(AcetoxyMethyl)-5-(2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate;1-((2R,3R,4R,5R)-3,4-Diacetyl-3,4-dihydroxy-5-(1-hydroxy-2-oxopropyl)tetrahydrofuran-2-yl)pyrimid
• CAS NO: 4105-38-8
• Molecular Formula: C₁₅H₁₈N₂O₉
• Molecular Weight: 370.31
• EINECS: 223-881-5
• Mol File: 4105-38-8.mol
• Article Data: 61

Chemical Properties

• Melting Point: 127.0 to 131.0 °C
• Appearance: /
• Density: 1.43 g/cm³
• Refractive Index: 1.552
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
• PKA: 9.39±0.10(Predicted)
• CAS DataBase Reference: 2',3',5'-Tri-O-acetyluridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',5'-Tri-O-acetyluridine(4105-38-8)
• EPA Substance Registry System: 2',3',5'-Tri-O-acetyluridine(4105-38-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 4105-38-8(Hazardous Substances Data)

Usage

Description

Uridine triacetate is an orally available pro-drug of uridine approved by the FDA for the treatment of the rare autosomal recessive disorder called hereditary orotic aciduria. The drug was also approved for treating overdose of two chemotherapies (fluorouracil and capecitabine). Uridine triacetate was developed by Wellstat Therapeutics and licensed to BTG.

Chemical Properties

White or almost white crystalline powder

Uses

2’,3’,5’-Triacetyluridine is used in the treatment of Alzheimer’s disease in mice and provide neuroprotective effects. Shown to also decrease depressive symptoms and increases in brain pH bipolar patients.

Definition

ChEBI: An acetate ester that is uracil in which the three hydroxy hydrogens are replaced by acetate group. A prodrug for uridine, it is used for the treatment of hereditary orotic aciduria and for management of fluorouracil toxicity.

Synthesis

Commercially available uridine (167) was treated with acetic anhydride in the presence of catalytic boron trifluoride-etherate, and the crude product was recrystallized from ethanol to give uridine triacetate (XX) in 74-78% yield.

InChI:InChI=1/C15H18N2O9/c1-7(18)23-6-10-12(24-8(2)19)13(25-9(3)20)14(26-10)17-5-4-11(21)16-15(17)22/h4-5,10,12-14H,6H2,1-3H3,(H,16,21,22)

Upstream product

• 108-24-7 acetic anhydride 
• 58-96-8 uridine 
• 73416-11-2 bis-trimethylsilyluracil 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 75-36-5 acetyl chloride 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 121524-02-5 phenyl-(tri-O-acetyl-1-thio-ξ-D-riboside) 
• 67-56-1 methanol 
• 55003-25-3 4-thio-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-(3H)-pyrimidine-2,4-dione 
• 71-23-8 propan-1-ol 
• 64-17-5 ethanol 
• 71-36-3 butan-1-ol 
• 117901-67-4 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2,4-dioxo-3-tritylsulfanyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 82913-19-7 [(2R,3R,4R)-3,4-diacetoxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate 

Downstream Products

• 98889-52-2 5-(4-nitrobenzene)sulfenyl-2',3',5'-tri-O-acetyluridine 
• 98889-50-0 5-(4-toluene)sulfenyl-2',3',5'-tri-O-acetyluridine 
• 93960-48-6 2',3',5'-tri-O-acetyl-4-O-(2,4,6-triisopropylbenzenesulfonyl)-uridine 
• 135067-73-1 5-phenylselenenyl-(2',3',5'-tri-O-acetyl)uridine 
• 108782-93-0 4-O-(2,4,6-trimethylphenyl)uridine 
• 98889-48-6 N-3-(2-nitro-4-toluene)sulfenyl-2',3',5'-tri-O-acetyluridine 
• 144102-56-7 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{3-[bis-(4-methoxy-phenyl)-methyl]-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl}-tetrahydro-furan-3-yl ester 
• 117901-67-4 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2,4-dioxo-3-tritylsulfanyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 102093-87-8 O⁴-(4-nitrophenylsulfonylethyl)uridine 
• 93960-47-5 N³-benzyl-2',3',5'-tri-O-acetyluridine 
• 98917-54-5 N-3-(2,4-dinitrobenzene)sulfenyl-2',3',5'-tri-O-acetyluridine 
• 76887-37-1 4-(3-nitro-1,2,4-triazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-pyrimedin-2(1H)-one 
• 31077-36-8 O^2'_,O3'_,O5'-triacetyl-3-benzoyl-uridine 
• 93960-46-4 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[3-(4-methoxy-benzoyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 

Relevant articles and documents

Anomalous interaction of tri-acyl ester derivatives of uridine nucleoside with a l-α-dimyristoylphosphatidylcholine biomembrane model: a differential scanning calorimetry study

Objectives: Uridine was conjugated with fatty acids to improve the drug lipophilicity and the interaction with phospholipid bilayers. Methods: The esterification reaction using carbodiimides compounds as coupling agents and a nucleophilic catalyst allowed us to synthesize tri-acyl ester derivatives of uridine with fatty acids. Analysis of molecular interactions between these tri-acyl ester derivatives and l-α-dimyristoylphosphatidylcholine (DMPC) multilamellar vesicles (MLV) – as a mammalian cell membrane model – have been performed by differential scanning calorimetry (DSC). Key findings: The DSC thermograms suggest that nucleoside and uridine triacetate softly interact with phospholipidic multilamellar vesicles which are predominantly located between the polar phase, whereas the tri-acyl ester derivatives with fatty acids (myristic and stearic acids) present a strongly interaction with the DMPC bilayer due to the nucleoside and aliphatic chains parts which are oriented towards the polar and lipophilic phases of the phospholipidic bilayer, respectively. However, the effects caused by the tri-myristoyl uridine and tri-stearoyl uridine are different. Conclusions: We show how the structural changes of uridine modulate the calorimetric behaviour of DMPC shedding light on their affinity with the phospholipidic biomembrane model.

Chemoenzymatic synthesis of Park's nucleotide: toward the development of high-throughput screening for MraY inhibitors

An efficient chemoenzymatic synthesis of UDP-N-acetylmuramyl-l-alanyl-γ-d-glutamyl-meso-diaminopimelyl-d-alanyl-d-alanine (Park's nucleotide) is reported. UDP-MurNAc is efficiently synthesized by a minimum number of protecting strategies. One-pot amino ac

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Anti-hepatitis B virus compound as well as preparation method and application thereof

The invention provides an anti-hepatitis B virus compound and a preparation method and application thereof, the compound is 4-thiouridine isobutyrate, the molecular formula is C13H18N2O6S, and the structural formula is shown in the specification. The compound provided by the invention can effectively inhibit the activity of hepatitis B virus, can be used as a substitute drug for lamivudine and telbivudine, solves the problem of drug resistance of lamivudine and the like in the aspect of resisting hepatitis B virus, is high in drug effect, low in toxicity and low in price, and provides a direction for development of drugs for treating hepatitis B. In addition, the invention discloses a preparation method of the compound 4-thiouridine isobutyrate, and the preparation method is mild in condition, easy to synthesize and suitable for industrial production.

Stereoselective Synthesis of Highly Functionalized Arabinosyl Nucleosides through Application of an N-Nitro Protecting Group

2′-Deoxy-2′,5-disubstituted arabinosyl uridine derivatives bearing a halogen (Cl, Br or I) at C2′ and an ethynyl group at C5 have been synthesized in 6 steps from 2′,3′,5′-tri-O-acetyl-5-iodo-uridine in overall yields of 61% (compound 3, Cl), 47% (compound 4, Br), and 19% (compound 5, I). Stabilization of a 2′-O-triflyl leaving group intermediate to overcome spontaneous intramolecular 2,2′-anhydro uridine formation was pivotal to the synthesis. Specifically, to favor SN2 reaction with a halogen nucleophile over intramolecular cyclization, the nucleophilicity of O-2 oxygen was reduced by incorporation of an adjacent electron withdrawing nitro substituent at N-3. The introduction of the 3-N-nitro group proceeded rapidly (nitronium trifluoroacetate, 1 min) and in quantitative yield. A one-pot method to remove the 3-N-nitro group by reductive nitration (zinc metal in acetic acid, 5 min) and the silyl protecting groups of the alkyne and 3′,5′ hydroxyls (fluoride reagent, 16 h) was established as the final synthetic step. This application of the 3-N-nitro protecting group addresses the significant shortfalls of the conventional approach to synthesis of 2′ modified nucleosides, wherein condensation of a 2′ modified sugar fragment with a pyrimidine base provides poor stereocontrol of N-glycosylation, low yields and incompatibility with 2′ iodo sugars.