Issue 19, 2009

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
29 Jun 2009
Accepted
20 Jul 2009
First published
30 Jul 2009

Org. Biomol. Chem., 2009,7, 3910-3913

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

M. Fiore, A. Chambery, A. Marra and A. Dondoni, Org. Biomol. Chem., 2009, 7, 3910 DOI: 10.1039/B912686D

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