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

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

Uses

Used in Pharmaceutical Industry:
2',3',5'-Tri-O-acetyl-5-hydroxymethyl uridine is used as a nucleoside analogue for its potential antiviral properties. It has been investigated for its role in inhibiting viral replication, making it a promising candidate for the development of antiviral drugs.
Used in RNA Modification:
2',3',5'-Tri-O-acetyl-5-hydroxymethyl uridine is used as a building block for RNA modification. Its unique structure allows for the alteration of RNA properties, which can be utilized in various applications, such as improving the stability and functionality of RNA molecules.
Used in Nucleic Acid Synthesis:
2',3',5'-Tri-O-acetyl-5-hydroxymethyl uridine is used as a key component in the synthesis of nucleic acids. Its modified structure can contribute to the development of novel nucleic acid-based therapeutics and diagnostic tools.

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.

Synthesis of aminoglycoside-modified oligonucleotides

(matrix presented) To study the structural requirements of aminoglycoside binding to nucleic acids, compound 1 - an analogue of the naturally occurring nucleoside J - was synthesized. When incorporated into oligodeoxynucleotides, 1 leads to thermal stabil