Formation and reactivity of 2,4-ditriazolyl pyrimidine C-nucleoside derived from pseudouridine.
Thymine and 2',3',5'-tri-O-acetyl-psi-uridine (1) was converted into the corresponding 2,4-ditriazolyl derivatives 5 and 2, respectively. Of these two substituents, the C4-triazolyl group was found to be quite susceptible to nucleophilic substitution while the other triazolyl is resistant.
Dyatkina
N
N
Codon Pharmaceuticals, Inc., Gaithersburg, MD 20877, USA.
Khorlin
A
A
Watanabe
K A
KA
D005021:Ethylamines; D009682:Magnetic Resonance Spectroscopy; D017553:Phosphorus Compounds; D011560:Pseudouridine / Q000737:chemistry*; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
C412234:2,4-di-(1,2,4-triazol-1-yl)-5-(2,3,5-tri-O-acetylribofuranosyl)pyrimidine; D005021:Ethylamines; D017553:Phosphorus Compounds; D011741:Pyrimidine Nucleosides; D014230:Triazoles; D011560:Pseudouridine; C045575:1,2,4-triazole; C013196:phosphoryl chloride; C016162:triethylamine