Abstract 1,3-Dipolar cycloaddition of dipolarophiles (1) and (2) with endocyclic heterocyclic azomethine ylides (4), (14) and (24), prepared in situ, leads to the protected β-and α-C-nucleo-sides (7), (8), (17), (18), (27) and (28), respectively. These, on subsequent hydrolysis, provide the corresponding C-nucleosides. The structures of all the synthesized com pounds are con firmed through analytical and spectral data. The assignment of configuration at C -1′ position of the C-nucleosides could be done by a comparative study of the properties of the corresponding α and β anomers with a reasonable degree of certainity.