Design and synthesis of 2'-deoxy-2'-[(1,2,3)triazol-1-yl]uridines using click chemistry approach.

A series of novel nucleosides bearing a 1,2,3-triazole moiety at the 2'-position of the sugar moiety has been synthesized starting from 2'-azidouridine and using the copper (I)-catalyzed Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition reaction. The reactions proceeded in overall yield of 52-82% and gave almost exclusively the 1,4-disubstituted 1,2,3-triazoles. The 2'-azidouridine was synthesized from uridine in two steps, and reacted with a variety of differently substituted alkynes to give the desired 2'-triazole-substituted uridine derivatives.