Single and dual glycoside clustering around calix[4]arene scaffolds via click thiol-ene coupling and azide-alkyne cycloaddition

We present the first synthesis of calix[4] arene-based S-glycoclusters via photoinduced multiple thiol-ene coupling of tetra-and octa-allyl calix[4]arenes with peracetylated glucosyl thiol (67-88% yields). Moreover we describe the dual clustering at the upper and lower rim of a calix[4] arene with two different sugars (galactose and glucose) via sequential copper(I)-catalyzed azide-alkyne cycloaddition and photoinduced thiol-ene coupling.