[(2R,3R,4S,5S)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3R,4S,5S)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS No.: 4105-38-8
• Molecular Formula: C15H18N2O9
• Molecular Weight: 370.316
• Hs Code.: 29349990
• European Community (EC) Number: 223-881-5
• Wikipedia: Uridine_triacetate
• Mol file: 4105-38-8.mol

Synonyms:4105-38-8

Chemical Property of [(2R,3R,4S,5S)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate

Chemical Property:

• Appearance/Colour: white or almost white crystalline powder
• Melting Point: 124-134oC
• Refractive Index: 1.552
• PKA: 9.39±0.10(Predicted)
• PSA: 142.99000
• Density: 1.43 g/cm³
• LogP: -1.13950
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 370.10123016
• Heavy Atom Count: 26
• Complexity: 660

Purity/Quality:

99% ^*data from raw suppliers

Tau ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(O1)N2C=CC(=O)NC2=O)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H](O1)N2C=CC(=O)NC2=O)OC(=O)C)OC(=O)C
• 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.
• 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.

Technology Process of [(2R,3R,4S,5S)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate

There total 48 articles about [(2R,3R,4S,5S)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

acetic anhydride (108-24-7) + uridine (58-96-8) → Tri-O-acetyluridine (4105-38-8)

Guidance literature:

With dmap;

DOI:10.1021/jo9822939

Reference yield: 100.0%

N3-benzyloxymethyl-2',3',5'-tri-O-acetyl uridine (116393-66-9) → Tri-O-acetyluridine (4105-38-8)

Guidance literature:

With trifluoroacetic acid; at 25 ℃; for 24h;

Reference yield: 98.0%

2,3,5-tri-O-acetyl-D-ribofuranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate (942428-91-3) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → Tri-O-acetyluridine (4105-38-8)

Guidance literature:

uracil; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 20 ℃; for 0.5h;

2,3,5-tri-O-acetyl-D-ribofuranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2008.06.042

upstream raw materials:

acetic anhydride

uridine

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

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

Downstream raw materials:

2',3',5'-Tri-O-acetyluridin-Vinylencarbonat-Addukt

2',3',5'-tri-O-acetyl-5-fluorouridine

5-(4-nitrobenzene)sulfenyl-2',3',5'-tri-O-acetyluridine

5-(4-toluene)sulfenyl-2',3',5'-tri-O-acetyluridine

Refernces

• 1、 Gmeiner,Anderson,Sahasrabudhe. "NMR studies show monomeric 5-fluorouridine forms base pairs of increased stability compared with uridine in non-aqueous solvents". . p. 2329 - 2344. Retrieved 1994.
• 2、 Baral, Bharat,Kumar, Pawan,Anderson, Brooke A.,?stergaard, Michael E.,Sharma, Pawan K.,Hrdlicka, Patrick J.. "Optimized synthesis of [3-15N]-labeled uridine phosphoramidites". . p. 5850 - 5852. Retrieved 2009.
• 3、 Serra, Carme,Farras, Jaume,Vilarrasa, Jaume. "Cyclic sulfates as synthetic equivalents of α-epoxynucleosides". . p. 9111 - 9113. Retrieved 1999.
• 4、 Gong, Yong,Chen, Lu,Zhang, Wei,Salter, Rhys. "Transglycosylation in the Modification and Isotope Labeling of Pyrimidine Nucleosides". supporting information. p. 5577 - 5581. Retrieved 2020/07/24.