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

Abstract

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.