A Convergent Strategy for the Synthesis of Second-Generation Iminosugar Clusters Using “Clickable” Trivalent Dendrons

Antoine Joosten (1) , Jérémy Schneider (1) , Mathieu Lepage (1) , Celine Tarnus (1) , Anne Bodlenner (1) , Philippe Compain (1)

1 LCM - Laboratoire de chimie moléculaire

A convergent strategy to access high‐valency iminosugar clusters based on two successive CuI‐catalysed azide–alkyne cycloadditions is reported. The key step of this approach relies on the grafting of azide‐armed trivalent iminosugar dendrons onto polyalkyne “clickable” scaffolds, thus tripling their initial valency. As a proof of concept, the synthesis of cyclodextrin‐based clusters containing the highest number of peripheral iminosugar ligands reported to date has been achieved. Evaluation of these compounds as mannosidase inhibitors revealed one of the strongest multivalent effects observed so far in glycosidase inhibition.

Domains: Chemical Sciences

Antoine Joosten, Jérémy Schneider, Mathieu Lepage, Celine Tarnus, Anne Bodlenner, et al.. A Convergent Strategy for the Synthesis of Second-Generation Iminosugar Clusters Using “Clickable” Trivalent Dendrons. European Journal of Organic Chemistry, 2014, 2014 (9), pp.1866-1872. ⟨10.1002/ejoc.201301583⟩. ⟨hal-02548519⟩