Abstract
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 language | English |
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Article number | e202101537 |
Number of pages | 12 |
Journal | European Journal of Organic Chemistry |
Volume | 2022 |
Issue number | 33 |
DOIs | |
Publication status | Published - 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.
Keywords
- Cone calix/1,3-alt thiacalixarene
- Heteroglycoclusters
- N-acylhydrazone
- N-alkyl-N-acylhydrazone
- Orthogonal chemistry