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2',3',5'-Tri-O-acetyluridine

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2',3',5'-Tri-O-acetyluridine 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:
4105-38-8
MF:
C15H18N2O9
MW:
370.31
EINECS:
223-881-5
Mol File:
4105-38-8.mol
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2',3',5'-Tri-O-acetyluridine Chemical Properties

Melting point:
127.0 to 131.0 °C
Density 
1.43±0.1 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
pka
9.39±0.10(Predicted)
InChIKey
AUFUWRKPQLGTGF-QRMSVCKNSA-N
CAS DataBase Reference
4105-38-8(CAS DataBase Reference)
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Safety Information

Safety Statements 
24/25
WGK Germany 
3
HS Code 
29349990

MSDS

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2',3',5'-Tri-O-acetyluridine Usage And Synthesis

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

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.

Chemical 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.

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