285549-57-7

Basic information

• Product Name: 2',3',5'-Tri-O-acetyl-5-hydroxyMethyl uridine
• Synonyms: 2',3',5'-Tri-O-acetyl-5-hydroxyMethyl uridine;5-(hydroxymethyl)-2',3',5'-triacetateuridine;5-(Hydroxymethyl)uridine 2',3',5'-triacetate
• CAS NO: 285549-57-7
• Molecular Formula: C₁₆H₂₀N₂O₁₀
• Molecular Weight: 400.3374
• Mol File: 285549-57-7.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• PKA: 9.01±0.10(Predicted)
• CAS DataBase Reference: 2',3',5'-Tri-O-acetyl-5-hydroxyMethyl uridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',5'-Tri-O-acetyl-5-hydroxyMethyl uridine(285549-57-7)
• EPA Substance Registry System: 2',3',5'-Tri-O-acetyl-5-hydroxyMethyl uridine(285549-57-7)

Safety Data

• Hazardous Substances Data: 285549-57-7(Hazardous Substances Data)

Usage

General Description

2',3',5'-Tri-O-acetyl-5-hydroxymethyl uridine is a chemical compound that belongs to the class of uridine derivatives. It is a modified form of uridine with three acetyl groups attached to the 2', 3', and 5' positions, as well as a hydroxymethyl group at the 5' position. 2',3',5'-Tri-O-acetyl-5-hydroxymethyl uridine has been studied for its potential therapeutic properties, particularly in the field of nucleoside analogues and antiviral drug development. It has been investigated for its role in inhibiting viral replication and for its potential as a treatment for viral infections. Additionally, it has also been studied for its potential use in RNA modification and as a building block for the synthesis of nucleic acids.

Upstream product

• 4433-40-3 5-hydroxymethyl uracil 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 194474-73-2 2′,3′,5′-tri-O-acetyl-5-nitrouridine 
• 4105-38-8 Tri-O-acetyluridine 
• 105659-31-2 5-bromo-2’,3’,5’-tri-O-acetyluridine 

Downstream Products

• 285549-58-8 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl}-tetrahydro-furan-3-yl ester 
• 285549-59-9 5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 285549-61-3 5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-((2R,3aS,9aR)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione 
• 285549-60-2 5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione 

Relevant articles and documents

Transglycosylation in the Modification and Isotope Labeling of Pyrimidine Nucleosides

Transglycosylation of pyrimidine nucleosides is demonstrated in a one-pot synthesis of uridine derivatives under microwave irradiation. Inductive activation of 2′,3′,5′-tri-O-acetyl uridine with a 5-nitro group produces a more-reactive glycosyl donor. Under optimized Vorbrüggen conditions, the 5-nitrouridine facilitates a reversible nucleobase exchange with a series of 5-substituted uracils. The protocol is also exemplified in a gram-scale reaction under thermal heating. The strategy provides easy access to isotopically labeled uridine.