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Peer-reviewedCC BY 4.0Chemistry (Weinheim an Der Bergstrasse, Germany)

N‐Sulfonyl Azalevoglucosan: A Versatile Platform for the Synthesis of Polysubstituted Piperidines

  • Dylan Yorga1
  • Jérôme Marrot2
  • Ana Poveda3,4,5,6
  • Nicolas Auberger1
  • Jesús Jiménez‐Barbero3,4,5,6
  • Jérôme Désiré1
  • Yves Blériot1
6 affiliations
  1. 1Groupe Glycochimie, Equipe OrgaSynth, IC2MP‐UMR CNRS 7285 Université de Poitiers Poitiers cedex France
  2. 2Institut Lavoisier de Versailles, UVSQ, CNRS, UMR 8180 Université Paris‐Saclay Versailles cedex France
  3. 3ClC bioGUNE Basque Research and Technology Alliance (BRTA) Derio Spain
  4. 4Ikerbasque Basque Foundation for Science Bilbao Spain
  5. 5Department of Organic & Inorganic Chemistry, Faculty of Science and Technology University of the Basque Country EHU‐UPV Leioa Spain
  6. 6Centro de Investigacion Biomédica En Red De Enfermedades Respiratorias Madrid Spain
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Abstract

Substituted piperidines are key synthetic fragments for designing drugs and play a significant role in the pharmaceutical industry. The reported synthetic methods allow access to mono‐, di‐, and tri‐substituted piperidines, but tetra‐ and penta‐substituted piperidines are scarce in the literature. In this study, exploiting the inherent chirality of iminosugars, we report the synthesis of a levoglucosan mimic in which the endocyclic oxygen of the pyranose ring has been replaced by a N‐sulfonyl group. The trans diaxial arrangement of its hydroxyl groups allows navigation on the piperidine ring to iteratively install functional groups at C1, C2, C3, C4, and C6 positions using simple experimental protocols with minimal protecting group manipulation. The broad functional group scope combined with the high regio‐ and stereo‐selectivity make this approach an appealing process for diversity‐oriented synthesis of polysubstituted piperidines, including modified iminosugars. We expect this platform will support drug discovery efforts to accelerate the discovery of therapeutically relevant molecules.

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Cite

BibTeXRIS
BibTeX
@article{yorga2026nsulfonyl,
  title = {{N‐Sulfonyl Azalevoglucosan: A Versatile Platform for the Synthesis of Polysubstituted Piperidines}},
  author = {Dylan Yorga and Jérôme Marrot and Ana Poveda and Nicolas Auberger and Jesús Jiménez‐Barbero and Jérôme Désiré and Yves Blériot},
  journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
  year = {2026},
  month = jul,
  doi = {10.1002/chem.71491},
  url = {https://doi.org/10.1002/chem.71491},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - N‐Sulfonyl Azalevoglucosan: A Versatile Platform for the Synthesis of Polysubstituted Piperidines
AU  - Dylan Yorga
AU  - Jérôme Marrot
AU  - Ana Poveda
AU  - Nicolas Auberger
AU  - Jesús Jiménez‐Barbero
AU  - Jérôme Désiré
AU  - Yves Blériot
PY  - 2026
DA  - 2026/07/28
JO  - Chemistry (Weinheim an Der Bergstrasse, Germany)
DO  - 10.1002/chem.71491
UR  - https://doi.org/10.1002/chem.71491
AB  - Substituted piperidines are key synthetic fragments for designing drugs and play a significant role in the pharmaceutical industry. The reported synthetic methods allow access to mono‐, di‐, and tri‐substituted piperidines, but tetra‐ and penta‐substituted piperidines are scarce in the literature. In this study, exploiting the inherent chirality of iminosugars, we report the synthesis of a levoglucosan mimic in which the endocyclic oxygen of the pyranose ring has been replaced by a N‐sulfonyl group. The trans diaxial arrangement of its hydroxyl groups allows navigation on the piperidine ring to iteratively install functional groups at C1, C2, C3, C4, and C6 positions using simple experimental protocols with minimal protecting group manipulation. The broad functional group scope combined with the high regio‐ and stereo‐selectivity make this approach an appealing process for diversity‐oriented synthesis of polysubstituted piperidines, including modified iminosugars. We expect this platform will support drug discovery efforts to accelerate the discovery of therapeutically relevant molecules.
SN  - 0947-6539
SN  - 1521-3765
ER  -