Access to a new type of homo-C-nucleosides with a 'split' 8-deazapurine via a 1,3-dipolar cycloaddition reaction

Abstract

Upon a 1,3-dipolar addition reaction with trimethylsilyl acetylene, azides (R,S)-7 were converted to the triazoles (R,S)-8. These diastereoisomers were separated and individually protodesilylated to yield (R)- and (S)-9, fully characterized by NMR. Structural assignments of unsaturated side compounds were deduced from a QUIET-NOESY experiment. Compounds (R)- and (S)-9 represent a new type of homo-C-nucleosides with a 'split' 8-azapurine base moiety.