157770-09-7

Basic information

• Product Name: 5’-O-4,4'-dimethoxytrityl-5-fluorouridine
• Synonyms: 5’-O-4,4'-dimethoxytrityl-5-fluorouridine
• CAS NO: 157770-09-7
• Molecular Weight: 564.567
• Mol File: 157770-09-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5’-O-4,4'-dimethoxytrityl-5-fluorouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5’-O-4,4'-dimethoxytrityl-5-fluorouridine(157770-09-7)
• EPA Substance Registry System: 5’-O-4,4'-dimethoxytrityl-5-fluorouridine(157770-09-7)

Safety Data

• Hazardous Substances Data: 157770-09-7(Hazardous Substances Data)

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 316-46-1 5-fluorouridine 

Downstream Products

• 157770-11-1 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-5-fluorouridine 
• 157770-10-0 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5-fluorouridine 
• 1338923-37-7 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-3'-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphino]-4-deoxo-3,4-dehydro-4-(2-cyanoethylthio)-5-fluorouridine 
• 1338923-36-6 5'-O-(4,4'-dimethoxytrityl)-2',3'-di-O-t-butyldimethylsilyl-4-deoxo-3,4-dehydro-4-(2-cyanoethylthio)-5-fluorouridine 
• 1338923-34-4 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-4-deoxo-3,4-dehydro-4-(2-cyanoethylthio)-5-fluorouridine 
• 1338923-35-5 5'-O-(4,4'-dimethoxytrityl)-3'-O-methyl-4-deoxo-3,4-dehydro-4-(2-cyanoethylthio)-5-fluorouridine 
• 1338923-33-3 5'-O-(4,4'-dimethoxytrityl)-2',3'-di-O-t-butyldimethylsilyl-5-fluoro-4-deoxo-3,4-dehydro-4-(1,2,4-triazol-1-yl)uridine 
• 1338923-32-2 5'-O-(4,4'-dimethoxytrityl)-4-deoxo-3,4-dehydro-4-(2-cyanoethylthio-)-5-fluorouridine 

Relevant articles and documents

Anti-flavivirus Activity of Different Tritylated Pyrimidine and Purine Nucleoside Analogues

A series of tritylated and dimethoxytritylated analogues of selected pyrimidine and purine nucleosides were synthesized and evaluated for their in vitro inhibitory activity against two important members of the genus Flavivirus in the Flaviviridae family, the yellow fever (YFV) and dengue viruses (DENV). Among all compounds tested, the 5′-O-tritylated and the 5′-O-dimethoxytritylated 5-fluorouridine derivatives exerted potency against YFV. Interestingly in the series of purine analogues, the 5′O, N-bis-tritylated fludarabine derivative revealed strong inhibitory activity against DENV at μm concentrations, however significantly weaker potency against YFV.

Synthesis of 5'-O-(4,4'-Dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5-fluorouridine 3'-(Cyanoethyl N,N-diisopropylphosphoramidite) and Its Use in the Synthesis of RNA

5-Fluorouridine (FUrd) has been successfully converted to 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5-fluorouridine 3'-(cyanoethyl N,N-diisopropyl(phosphoramidite) by methods similar to those employed for the preparation of other ribonucleoside phosphoramidites.The desired product, as well as its precursors and the incorrect regioisomers, are prepared and fully characterized by 1H NMR, 19F NMR, 31P NMR, FAB-MS, UV absorbance, elemental analysis, and melting points.The purified material is used for the production of RNA by solid-phase methods.Coupling yields of 94percent are obtained with this material.The resulting RNA is readily purified and used for biophysical studies.The self-complemetary RNA decamer 5'-rGCGAAU(FU)CGC is prepared and purified.The material adopts an A-form duplex in solution at neutral pH as characterized by CD spectroscopy.The thermal stability of the duplex is similar to the parent duplex oligoribonucleotide prepared with uridine instead of 5-fluorouridine.The control duplex has a Tm of 53.8 and the FUrd substituted duplex has a Tm of 56.6 xb0 deg C as determined by UV hyperchromicity at 260 nm.The CD spectra and UV hyperchromicity data for the duplex oligoribonucleotide containing FUrd have a slight pH dependence indicating that ionization of FUrd has a slight but measurable impact on RNA duplex stability. 1D NMR spectroscopy of the imino hydrogens for this duplex in H2O solution confirms the formation of Watson-Crick base pairs.The imino hydrogen resonance for the FUrd-A base pair is moved downfield and broadened compared with a control duplex oligoribonucleotide as a consequence of the electron-withdrawing inductive effect of fluorine.