Synlett 2023; 34(16): 1866-1893
DOI: 10.1055/s-0042-1751449
account

From Sweet Molecular Giants to Square Sugars and Vice Versa

This work was funded by Université de Strasbourg (IDEX program R701/W15RPE19), the Centre National de la Recherche Scientifique (CNRS) (LIMA-UMR 7042), the Institut Universitaire de France (IUF) and the Fondation Jean-Marie Lehn (PCO-004-2020, PCO-003-2016).


Abstract

This account describes our recent studies in the field of glycomimetics. Our efforts in understanding the structural basis of multivalent effects in glycosidase inhibition have led to decisive mechanistic insights supported by X-ray diffraction analyses and to the discovery of multimeric iminosugars displaying one of the largest binding enhancements reported so far for a non-polymeric enzyme inhibitor. Pushing the limits of the inhibitory multivalent effect has also driven progress in synthetic methodology. The unexpected observation of side products en route to the synthesis of our targets has been the starting point of several new synthetic methodologies, including metal-free deoxygenation of alcohols and one-pot double thioglycosylation. In parallel to our work on ‘giant’ neoglycoclusters, we have developed access to original constrained glycomimetics based on a 4-membered ring (‘square sugars’). Carbohydrates with a quaternary (pseudo)anomeric position were also synthesized from exo-glycals through catalytic hydrogen atom transfer and a novel oxidative radical-polar crossover process.

1 Introduction

2 Sweet Giants

3 Multivalency Spin-Offs

4 Sweet Curiosities

4.1 Square Sugars

4.2 From C,C-Glycosides to Formal Glycosylation of Quinones

5 Conclusion



Publication History

Received: 08 March 2023

Accepted after revision: 05 April 2023

Article published online:
16 May 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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