4710-75-2

Usage

Uses

Used in RNA Research:
3',5'-Bis-O-(triphenylmethyl)uridine is used as a research tool for understanding the structure and function of RNA. 3',5'-Bis-O-(triphenylMethyl)uridine's ability to protect and later reveal the reactive hydroxyl groups of the uridine base is instrumental in studying RNA's properties and interactions.
Used in Chemical Biology:
In the field of chemical biology, 3',5'-Bis-O-(triphenylmethyl)uridine serves as a valuable compound for the development of new RNA-based technologies. Its protective Tr groups contribute to the compound's stability, facilitating its use in various experimental setups and applications.
Used in Medicinal Chemistry Research:
3',5'-Bis-O-(triphenylmethyl)uridine is utilized in medicinal chemistry for the synthesis of RNA-active molecules. 3',5'-Bis-O-(triphenylMethyl)uridine's protective features make it suitable for creating stable intermediates in the development of potential therapeutic agents targeting RNA molecules.
Used in Drug Development:
In the pharmaceutical industry, 3',5'-Bis-O-(triphenylmethyl)uridine is used as a precursor in the synthesis of drugs that target RNA. Its role in creating stable and well-defined RNA-active compounds is crucial for advancing the discovery and design of new medications.

InChI:InChI=1/C47H40N2O6/c50-41-31-32-49(45(52)48-41)44-42(51)43(55-47(37-25-13-4-14-26-37,38-27-15-5-16-28-38)39-29-17-6-18-30-39)40(54-44)33-53-46(34-19-7-1-8-20-34,35-21-9-2-10-22-35)36-23-11-3-12-24-36/h1-32,40,42-44,51H,33H2,(H,48,50,52)

Upstream product

• 76-83-5 trityl chloride 
• 6554-10-5 5'-O-trityluridine 
• 58-96-8 uridine 

Downstream Products

• 22860-36-2 (2R,3R,3aR,9aR)-3-Trityloxy-2-trityloxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 129885-88-7 1-(3,5-di-O-trityl-β-D-ribofuranosyl)-4-methoxy-2-pyrimidinone 
• 16731-30-9 1-<3,5-di-O-trityl-β-D-erythro-pentofuran-2-ulosyl>uracil 
• 129885-90-1 1-(2-deoxy-2-fluoro-3,5-di-O-trityl-β-D-ribofuranosyl)-4-methoxy-2-pyrimidinone 
• 129885-91-2 1-(2-deoxy-2-fluoro-3,5-di-O-trityl-β-D-ribofuranosyl)-N³-methyluracil 
• 129885-92-3 N³-methyl-1-(3,5-di-O-trityl-β-arabinofuranosyl)uracil 
• 38642-29-4 3'-O-trityluridine 
• 163011-98-1 (Z)-2'-deoxy-2'-ethoxycarbonylmethylene-3',5'-di-O-trityluridine 
• 163011-96-9 (Z)-2'-cyanomethylene-2'-deoxy-3',5'-di-O-trityluridine 
• 16731-36-5 N³-methyl-3',5'-di-O-trityluridine 

Relevant academic research and scientific papers

Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation

The disclosed invention is a composition for and a method of seating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (“RT-PCR”). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

In search of flavivirus inhibitors: Evaluation of different tritylated nucleoside analogues

Following up on a hit that was identified in a large scale cell-based antiviral screening effort, a series of triphenylmethyl alkylated nucleoside analogues were synthesized and evaluated for their in vitro antiviral activities against the dengue virus (DENV) and the yellow fever virus (YFV). Hereto, trityl moieties were attached at various positions of the sugar ring combined with subtle variations of the heterocyclic base. Several triphenylmethyl modified nucleosides were uncovered being endowed with submicromolar in vitro antiviral activity against the YFV. The most selective inhibitor in this series was 3′,5′-bis-O-tritylated-5-chlorouridine (1b) affording a selectivity index of over 90, whereas the 3′,5′-bis-O-tritylated inosine congener (5b) displayed the highest activity, but proved more toxic. The finding of these lipophilic structures being endowed with high antiviral activity for flaviviruses, should stimulate the interest for further structureeactivity research.

Stereospecific synthesis and anti-HIV activity of (Z)2'- and (E)3'- deoxy-2'(3')-C-(chloromethylene) pyrimidine nucleosides

Reaction of 1-[2,5(and 3,5)-di-O-trityl-β-D-erythro-pentofuran-3(and 2)- ulosyl]uracil derivatives 5 and 6 with (chloromethyl)triphenylphosphorane resulted in the stereoselective formation of (E)-3'- and (Z)-2'- chloromethylene derivatives 7 (69%) and 8 (53%), respectively, deprotection of which gave 9 and 10. Transformation of the uracil nucleoside 7 into cytosine one followed by deprotection yielded 12. The latter was convened into the arabinoside 14. The fully deprotected chloromethylene nucleosides were tested for their activity against HIV-1 and HIV-2.

Synthesis of Uridine Derivatives Containing Strategically Placed Radical Traps as Potential Inhibitors of Ribonucleotide Reductase

A series of uridine derivatives have been prepared with a view to inhibiting the enzyme ribonucleotide reductase by trapping the radical responsible for initiating the reduction.These have an oxime ether on the beta face at C-3 or C-2 of the ribose moiety

Nucleosides. LVI. Synthesis and chemical modifications of 3'-deoxy- pyrimidine nucleosides

3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O- toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert- butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterized by elemental analyses and UV and 1H-NMR spectra.