PURINE NUCLEOSIDES .27. SYNTHESIS OF I- AND 7-METHYL-8-OXOGUANOSINE AND RELATED NUCLEOSIDES . USE OF N-AMINO GROUP AS A SELECTIVE BLOCKING AGENT IN NUCLEOSIDE SYNTHESIS

The synthesis of the 9-β-d-ribofuranosyl derivative of 7-methyl-8-oxoguanine, a purine which appears in large quantities in the urine of leukemia patients, is described. Several related nucleosides, including the 1-methyl- and 7-dimethyl derivatives of 8-oxoguanosine and 1-methyl- and 7-methyl-8-oxoadenosine, have also been prepared. The first use of the N-amino function as a blocking group in the selective methylation of nucleosides is described. A method is reported for the resolution of N-H proton resonances in the presence of small amounts of water through the use of trifluoroacetic acid in [2H6]dimethyl sulfoxide. © 1969.