133128-06-0

Basic information

• Product Name: 5'-O-(4,4'-dimethoxytrityl)-α,α,α-trifluorothymidine
• Synonyms: 5'-O-(4,4'-dimethoxytrityl)-α,α,α-trifluorothymidine
• CAS NO: 133128-06-0
• Molecular Weight: 598.576
• Mol File: 133128-06-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 5'-O-(4,4'-dimethoxytrityl)-α,α,α-trifluorothymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-dimethoxytrityl)-α,α,α-trifluorothymidine(133128-06-0)
• EPA Substance Registry System: 5'-O-(4,4'-dimethoxytrityl)-α,α,α-trifluorothymidine(133128-06-0)

Safety Data

• Hazardous Substances Data: 133128-06-0(Hazardous Substances Data)

Upstream product

• 951-78-0 2'-deoxyuridine 
• 40615-35-8 4,4'-dimethoxytrityl alcohol 
• 70-00-8 2'-deoxy-5-trifluoromethyluridine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 

Downstream Products

• 1046113-67-0 5-trifluoromethyl-3'-O-(3-carboxypropionyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine 
• 133100-90-0 5'-O-(4,4'-dimethoxytrityl)-3'-O-(methyl phosphor-N,N-diisopropylamidite)-α,α,α-trifluorothymidine 

Relevant articles and documents

Triplex- and duplex-forming abilities of oligonucleotides containing 2′-deoxy-5-trifluoromethyluridine and 2′-deoxy-5-trifluoromethylcytidine

A facile synthesis of 2′-deoxy-5-trifluoromethyluridine and 2′-deoxy-5-trifluoromethylcytidine phosphoramidites from commercially available 2′-deoxyuridine and 2′-deoxycytidine was achieved, respectively. The obtained phosphoramidites were incorporated into oligonucleotides, and their binding affinity to double-stranded DNA (dsDNA) and single-stranded RNA (ssRNA) was evaluated by UV-melting experiments. The triplex-forming abilities of oligonucleotides including 5-trifluoromethylpyrimidine nucleobases with dsDNA were decreased. Especially, the stability of the triplex containing a trifluoromethylcytosine (CF3C)-GC base triplet was low, likely due to the low pKa of protonated CF3C by the electron-withdrawing trifluoromethyl group. A slight decrease in stability of the duplex formed with ssRNA by oligonucleotides including 5-tri-fluoromethylpyrimidine nucleobases was only observed, suggesting that they might be applicable to various ssRNA-targeted technologies using features of fluorine atoms.

Improved synthesis of 5-hydroxymethyl-2′-deoxycytidine phosphoramidite using a 2′-deoxyuridine to 2′-deoxycytidine conversion without temporary protecting groups

5-Hydroxymethylcytosine has recently been characterized as the 'sixth base' in human DNA. To enable research on this DNA modification, we report an improved method for the synthesis of 5-hydroxymethyl-2′-deoxycytidine (5-HOMedC) phosphoramidite for site-specific incorporation into oligonucleotides. To minimize manipulations we employed a temporary protecting group-free 2′-deoxyuridine to 2′-deoxycytidine conversion procedure that utilizes phase transfer catalysis. The desired 5-HOMedC phosphoramidite is obtained in six steps and 24% overall yield from 2′-deoxyuridine.

Synthesis, Annealing Properties, 19F NMR Characterization, and Detection Limits of a Trifluorothymidine-Labeled Antisense Oligodeoxyribonucleotide 21 mer

The synthesis and characterization are described of trifluorothymidine groups incorporated into an antisense 21 mer designed to target gene sequences that encode serine proteases in T-lymphocytes. 1H NMR titration studies on 3',5'-O-TPDS-trifluorothymidin