Heteroglycoclusters through Unprecedented Orthogonal Chemistry Based on N-Alkylation of N-Acylhydrazone

Marwa Frey, David Mathiron, Serge Pilard, David Lesur, Rym Abidi, Thouraya Barhoumi-Slimi, Peter Cragg, Mohammed Benazza

Research output: Contribution to journalArticlepeer-review


Orthogonal chemistry is a valuable tool in the preparation of complex molecules as heteroglycoclusters. Unfortunately, selective heteroconjugation of multifunctional starting materials remains a usually challenging problem to overcome. Herein, we report the first report on harnessing N-alkylation of N-acylhydrazone as a key step in the orthogonal synthesis. Sequentially associated with the azido-alkyne click chemistry, it stands out as a new and straightforward synthetic method of glycoconjugate small molecules, heterodisaccharides, and heteroglycoclusters based on cone p-tBu-calix[4]arene and 1,3-alt p-tBu-thiacalix[4]arene with potential drug-like properties.
Original languageEnglish
Article numbere202101537
Number of pages12
JournalEuropean Journal of Organic Chemistry
Issue number33
Publication statusPublished - 9 Mar 2022

Bibliographical note

Funding Information:
Support from the LG2 A‐UMR7378‐CNRS research group is gratefully acknowledged. M. Fray was financially supported by a scholarship from the Tunisian government.

Publisher Copyright:
© 2022 Wiley-VCH GmbH.


  • Cone calix/1,3-alt thiacalixarene
  • Heteroglycoclusters
  • N-acylhydrazone
  • N-alkyl-N-acylhydrazone
  • Orthogonal chemistry


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