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The synthesis of (2-deoxy-3,5-bis(O-(p-toluoyl))-α-D-ribofuranosyl)ethyne 5 by reaction of ethynylmagnesium bromide with 2-deoxy-3,5-bis(O-(p-toluoyl))-α-D-ribofuranosyl chloride 2 is reported. The resulting C-glycoside precursor 5 undergoes (4+2)- as well as (3+2)-cycloaddition reactions to give 5- and 6-membered heterocyclic C-glycosides.

Synthesis and cycloaddition reactions of [2-deoxy-3,5-bis[O-(p-toluoyl)]-α-D-ribofuranosyl]ethyne