6554-11-6

Usage

Uses

Used in Biochemical Research:
2',5'-Bis-O-(triphenylmethyl)uridine is used as a protected nucleoside for biochemical research purposes. The Trityl groups attached to the 2' and 5' positions protect the uridine from degradation, allowing for more stable and reliable experiments.
Used in Synthesis of Modified Nucleic Acids:
2',5'-Bis-O-(triphenylmethyl)uridine is used as a building block in the synthesis of modified nucleic acids. The protection provided by the Trityl groups allows for the incorporation of the modified uridine into larger nucleic acid structures without unwanted side reactions.
Used in Study of Modified Nucleosides:
2',5'-Bis-O-(triphenylmethyl)uridine is used as a model compound in the study of modified nucleosides. The altered base-pairing and hydrogen bonding properties due to the Trityl groups provide insights into the effects of such modifications on the structure and function of nucleic acids.
Used in Pharmaceutical Development:
2',5'-Bis-O-(triphenylmethyl)uridine is used as a starting material in the development of new pharmaceuticals targeting RNA-based therapeutics. The modified uridine can be incorporated into drug candidates to modulate their interactions with RNA molecules, potentially leading to novel treatments for various diseases.

InChI:InChI=1/C47H40N2O6/c50-41-31-32-49(45(52)48-41)44-43(55-47(37-25-13-4-14-26-37,38-27-15-5-16-28-38)39-29-17-6-18-30-39)42(51)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 
• 58-96-8 uridine 
• 14470-28-1 mono-4-methoxytrityl chloride 
• 6554-10-5 5'-O-trityluridine 

Downstream Products

• 56889-16-8 3'-O-mesyl-2',5'-di-O-trityluridine 
• 38642-28-3 2,3'-anhydro-1-(2,5-di-O-trityl-β-D-xylofuranosyl)uracil 
• 16731-34-3 2',5'-di-O-trityl-1-(β-D-xylofuranosyl)uracil 
• 38642-15-8 2'-O-Trityluridine 
• 129885-93-4 1-(3-deoxy-3-fluoro-2,5-di-O-trityl-β-D-xylofuranosyl)-N³-methyluracil 
• 16731-35-4 1-(O²,O⁵-ditrityl-β-D-xylofuranosyl)-3-methyl-1H-pyrimidine-2,4-dione 
• 16731-37-6 1-<2,5-di-O-trityl-β-D-erythro-pentofuran-3-ulosyl>uracil 
• 129885-94-5 1-(2,5-di-O-trityl-β-D-ribofuranosyl)-4-methoxy-2-pyrimidinone 
• 38642-28-3 (1R,9R,10R,12R)-12-Trityloxy-10-trityloxymethyl-8,11-dioxa-2,6-diaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one 
• 129885-89-8 1-(3-deoxy-3-fluoro-2,5-di-O-trityl-β-D-xylofuranosyl)uracil 
• 161109-92-8 3'-O-phenoxythiocarbonyl-2',5'-di-O-trityluridine 
• 4566-73-8 N³-methyl-2',5'-di-O-trityluridine 

Relevant academic research and scientific papers

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.

Synthesis of 2′-C-methylcytidine and 2′-C-methyluridine derivatives modified in the 3′-position as potential antiviral agents

As part of our anti-hepatitis C program, we recently discovered 2′-C-methylcytidine (1) and 2′-C-methyluridine (2), which are potent inhibitors in cell culture of several viruses (bovine viral diarrhea virus (BVDV), yellow fever virus (YFV)) closely relat

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.

Synthesis and Anticancer and Antiviral Activities of Various 2'- and 3'-Methylidene-Substituted Nucleoside Analogues and Crystal Structure of 2'-Deoxy-2'-methylidenecytidine Hydrochloride

Various 2'- and 3'-methylidene-substituted nucleoside analogues have been synthesized and evaluated as potential anticancer and/or antiviral agents.Among these compounds, 2'-deoxy-2'-methylidene-5-fluorocytidine (22) and 2'-deoxy-2'-methylidenecytidine (23) not only demonstrated potent anticancer activity in culture against murine L1210 and P388 leukemias, Sarcoma 180, and human CCRF-CEM lymphoblastic leukemia, producing ED50 values of 1.2 and 0.3 μM, 0.6 and 0.4 μM, 1.5 and 1.5 μM, and 0.05 and 0.03 μM, respectively, but also were active in mice against murine L1210 leukemia.Of all the tested drug dosage levels (25, 50, and 75 mg/kg, respectively) compound 23 had no toxic deaths and compound 22 yielded only one toxic death at the highest dosage level.On the contrary, in the same study, 1-β-D-arabinofuranosylcytosine (ara-C) resulted in 2/5, 5/5, and 5/5 toxic deaths, respectively.Both compounds 22 and 23 have shown better anticancer activity than ara-C, yielding higher T/C * 100 values and some long-term survivors ( > 60 days).In addition, compounds 22 and 23 were found to have, respectively, approximately 130 and 40 times lower binding affinity for cytidine/deoxycytidine deaminase derived from human KB cells compared to ara-C, suggesting that the two 2'-methylidene-substituted analogues may be more resistant to deamination.Cytoplasmic deoxycytidine kinase (dCK) was required for compounds 22 and 23 action.Furthermore, compounds 14, 22, 23, and 24 also have antiherpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) activity in cell culture.In addition, the crystal structure of 2'-deoxy-2'-methylidenecytidine hydrochloride (23*HCl) was determined by X-ray crystallography.