N-15 Double-Labeled Guanosine from Inosine through Ring-Opening-Ring-Closing and One-Pot Pd-Catalyzed C-O and C-N Cross-Coupling Reactions

作者：Caner Joaquim; Vilarrasa Jaume^*

来源：Journal of Organic Chemistry, 2010, 75(14): 4880-4883.

DOI：10.1021/jo100808w

[N,1-N-15(2)]-Guanosine, or [1,NH2-N-15(2)]-guanosine, and derivatives were prepared from tri-O-acetylinosine, via N-nitration and reaction with (NH2OH)-N-15, followed by conversion of the N-15-labeled 1-hydroxyinosine to the corresponding 2,6-dichloropurine riboside. The sequential one-pot C-O and C-N key couplings of this dichloro derivative with PhCH2OH and (PhCONH2)-N-15 or (PrCONH2)-Pr-i-N-15 was achieved in good overall yields, with Pd(0)-Xantphos as the best choice of five different catalytic systems examined.

• 出版日期2010-7-16