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PreprintCC BYChemRxiv

Stereoselective N-Glycosylation by Iron-Catalyzed Cross-Coupling of Glycosyl Phosphates

  • Shubhi Dwivedi
  • Sumeli Dasgupta
  • Abhijit Sau
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Abstract

Herein, we report an iron-catalyzed glycosyl cross-coupling strategy for stereoselective β-N-glycosylation through activation of glycosyl phosphate donors under mild conditions. Inspired by the reactivity of enzymes and the biological relevance of phosphate leaving groups, this biomimetic glycosyl phosphate enables efficient coupling of diverse Naglycones with both armed and disarmed sugars. The methodology exhibits broad substrate scope with excellent functional-group tolerance and high β-stereoselectivity. The synthetic utility of the protocol is demonstrated with over 58 examples, including late-stage functionalization of pharmaceutical and biologically relevant scaffolds, offering new opportunities to advance chemical biology, glycochemistry, and therapeutic discovery.

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Cite

BibTeXRIS
BibTeX
@misc{dwivedi2026stereoselective,
  title = {{Stereoselective N-Glycosylation by Iron-Catalyzed Cross-Coupling of Glycosyl Phosphates}},
  author = {Shubhi Dwivedi and Sumeli Dasgupta and Abhijit Sau},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15011051/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011051/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Stereoselective N-Glycosylation by Iron-Catalyzed Cross-Coupling of Glycosyl Phosphates
AU  - Shubhi Dwivedi
AU  - Sumeli Dasgupta
AU  - Abhijit Sau
PY  - 2026
DA  - 2026/10/26
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15011051/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011051/v1
AB  - Herein, we report an iron-catalyzed glycosyl cross-coupling strategy for stereoselective β-N-glycosylation through activation of glycosyl phosphate donors under mild conditions. Inspired by the reactivity of enzymes and the biological relevance of phosphate leaving groups, this biomimetic glycosyl phosphate enables efficient coupling of diverse Naglycones with both armed and disarmed sugars. The methodology exhibits broad substrate scope with excellent functional-group tolerance and high β-stereoselectivity. The synthetic utility of the protocol is demonstrated with over 58 examples, including late-stage functionalization of pharmaceutical and biologically relevant scaffolds, offering new opportunities to advance chemical biology, glycochemistry, and therapeutic discovery.
ER  -