Cu(I)-Catalyzed cycloaddition of constrained azido-alkynes: access to 12- to 17-membered monomeric triazolophanes incorporating furanoside rings

A strained monomeric 12-membered triazolophane was formed by the Cu(I)-catalyzed intramolecular cycloaddition of an azide to an alkyne having a constrained tether incorporating an aromatic ring and a furanoside ring. Similar cycloadditions of azido-alkynes having ester, furanoside and peptidic tethers led to the formation of monomeric triazolophanes of higher ring sizes.

Graphical abstractFuranoside ring- and peptide-appended azido-alkynes afforded monomeric 12- to 17-membered triazolophanes fused to furanoside rings via Cu(I)-catalyzed cycloaddition.Figure optionsDownload full-size imageDownload as PowerPoint slide