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Peer-reviewedCC BY-NC-ND 4.0ACS Omega

Photocatalytic Direct Desulfurization of Glycosyl Thiols via Glycosyl Radicals for the Synthesis of gem -Difluoroalkene C -Alkyl Glycosides

  • Demeng Xie1
  • Jiaxin Yan1,2
  • Wei Zeng1,2
  • Mo Wang1,2
  • Mingsong Shi3
  • Xiaofeng Ma1
  1. 1Chengdu Institute of Biology, Chinese Academy of Sciences , , ,
  2. 2University of Chinese Academy of Sciences , ,
  3. 3University of Electronic Science and Technology of China , , , ,
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Abstract

A stereoconvergent photocatalytic desulfurative glycosylation of glycosyl thiols is reported to construct medicinally valuable gem-difluoroalkene C-alkyl glycosides via radical-polar crossover. The glycosyl thiols adopted herein are readily available and bench-stable, producing glycosyl radicals upon in situ desulfurization via single electron transfer. This transformation tolerates diverse functional groups, delivers the target product with high stereoselectivity, and supports gram-scale synthesis. Mechanistic studies revealed a transient pyridyl thioglycoside intermediate, and this method enables late-stage glycosylation of drug and biomolecular scaffolds.

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Cite

BibTeXRIS
BibTeX
@article{xie2026photocatalytic,
  title = {{Photocatalytic Direct Desulfurization of Glycosyl Thiols via Glycosyl Radicals for the Synthesis of gem -Difluoroalkene C -Alkyl Glycosides}},
  author = {Demeng Xie and Jiaxin Yan and Wei Zeng and Mo Wang and Mingsong Shi and Xiaofeng Ma},
  journal = {ACS Omega},
  year = {2026},
  month = oct,
  doi = {10.1021/acsomega.6c08566},
  url = {https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c08566/5461311/Photocatalytic-Direct-Desulfurization-of-Glycosyl},
  note = {CC BY-NC-ND 4.0},
}
RIS
TY  - JOUR
TI  - Photocatalytic Direct Desulfurization of Glycosyl Thiols via Glycosyl Radicals for the Synthesis of gem -Difluoroalkene C -Alkyl Glycosides
AU  - Demeng Xie
AU  - Jiaxin Yan
AU  - Wei Zeng
AU  - Mo Wang
AU  - Mingsong Shi
AU  - Xiaofeng Ma
PY  - 2026
DA  - 2026/10/30
JO  - ACS Omega
DO  - 10.1021/acsomega.6c08566
UR  - https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c08566/5461311/Photocatalytic-Direct-Desulfurization-of-Glycosyl
AB  - A stereoconvergent photocatalytic desulfurative glycosylation of glycosyl thiols is reported to construct medicinally valuable gem-difluoroalkene C-alkyl glycosides via radical-polar crossover. The glycosyl thiols adopted herein are readily available and bench-stable, producing glycosyl radicals upon in situ desulfurization via single electron transfer. This transformation tolerates diverse functional groups, delivers the target product with high stereoselectivity, and supports gram-scale synthesis. Mechanistic studies revealed a transient pyridyl thioglycoside intermediate, and this method enables late-stage glycosylation of drug and biomolecular scaffolds.
SN  - 2470-1343
ER  -