3-(2’ - Tetrahydropyrannylthio) indole, VI, What's synthesized from 3-thioindole, X, by treatment with 2-chlorotetrahydropyran, VIIII, under basic conditions. This compound was used as a model system to study the feasibility of synthesizing biologically important C-nucleosides by first connecting the sugar to the base to a bridging sulfur atom and then extruding the sulfur atom with formation of the required carbon - carbon bond.