A new and efficient synthetic method for 15N3-labeled cytosine nucleosides: Dimroth rearrangement of cytidine N3-oxides.
The treatment of (15)N(4)-labeled cytidine N(3)-oxide and (15)N(4)-labeled 2'-deoxycytidine N(3)-oxide, prepared from the appropriate unprotected uridines in three reaction steps, with benzyl bromide in the presence of excess lithium methoxide allowed the smooth occurrence of their Dimroth rearrangement even under mild conditions leading to the corresponding (15)N(3)-labeled uridine 4-O-benzyloximes which can easily undergo the reductive N-O bond cleavage to give the desirable (15)N(3)-labeled cytosine nucleosides in high total yields.
Sako
Magoichi
M
Gifu Pharmaceutical University, 5-6-1, Mitahora-higashi, Gifu 502-8585, Japan. sako@gifu-pu.ac.jp
Kawada
Hiroyoshi
H
D002384:Catalysis; D003562:Cytidine / Q000737:chemistry*; D015394:Molecular Structure; D009587:Nitrogen Isotopes; D019906:Nuclear Magnetic Resonance, Biomolecular; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D014529:Uridine
D009587:Nitrogen Isotopes; D011741:Pyrimidine Nucleosides; D003562:Cytidine; D014529:Uridine