6554-11-6

Basic information

• Product Name: 2',5'-Bis-O-(triphenylMethyl)uridine
• Synonyms: 2',5'-Bis-O-(triphenylMethyl)uridine;2',5'-di-O-trityluridine;2',5'-Ditrityluridine;2',5'-O-Bis(triphenylmethyl)uridine;NSC 94674
• CAS NO: 6554-11-6
• Molecular Formula: C₄₇H₄₀N₂O₆
• Molecular Weight: 728.8303
• Mol File: 6554-11-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.33g/cm³
• Refractive Index: 1.705
• CAS DataBase Reference: 2',5'-Bis-O-(triphenylMethyl)uridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',5'-Bis-O-(triphenylMethyl)uridine(6554-11-6)
• EPA Substance Registry System: 2',5'-Bis-O-(triphenylMethyl)uridine(6554-11-6)

Safety Data

• Hazardous Substances Data: 6554-11-6(Hazardous Substances Data)

Usage

General Description

2',5'-Bis-O-(triphenylmethyl)uridine is a modified form of uridine, a nucleoside found in RNA. This chemical compound has two triphenylmethyl (Trityl) groups attached to the 2' and 5' positions of the uridine molecule. These bulky groups provide protection to the uridine from chemical and enzymatic degradation, making it useful for various biochemical and research applications. These modifications can also alter the base-pairing and hydrogen bonding properties of uridine, potentially affecting its interactions with other molecules. The compound is commonly used in the synthesis and study of modified nucleic acids and nucleosides for research purposes.

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

• 16731-35-4 1-(O²,O⁵-ditrityl-β-D-xylofuranosyl)-3-methyl-1H-pyrimidine-2,4-dione 
• 129885-93-4 1-(3-deoxy-3-fluoro-2,5-di-O-trityl-β-D-xylofuranosyl)-N³-methyluracil 
• 38642-15-8 2'-O-Trityluridine 
• 16731-34-3 2',5'-di-O-trityl-1-(β-D-xylofuranosyl)uracil 
• 38642-28-3 2,3'-anhydro-1-(2,5-di-O-trityl-β-D-xylofuranosyl)uracil 
• 56889-16-8 3'-O-mesyl-2',5'-di-O-trityluridine 
• 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 articles and documents

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.

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.