A new and efficient synthetic method for 15N3-labeled cytosine nucleosides: Dimroth rearrangement of cytidine N3-oxides
The treatment of 15N4-labeled cytidine N 3-oxide and 15N4-labeled 2′-deoxycytidine N3-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 15N 3-labeled uridine 4-O-benzyloximes which can easily undergo the reductive N-O bond cleavage to give the desirable 15N 3-labeled cytosine nucleosides in high total yields.
Oxidation of Cytosine and 5-Methylcytosine Nucleosides and 5-Methyl-2'-deoxycytidine 5'-Monophosphate with Peroxosulfate Ions
Reaction of 5-methylcytosine nucleosides and nucleotide with Na2S2O8 resulted in an oxidation of the 5-methyl group, while treatment of them and cytosine nucleosides with KHSO5 gave the corresponding N3-oxides.
Itahara, Toshio
p. 1591 - 1594
(2007/10/02)
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