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DOI: 10.1055/a-2149-4586
C-5 Epimerisation of d-Mannopyranosyl Fluorides: The Influence of Anomeric Configuration on Radical Reactivity
We thank the Australian Research Council for financial support (DP220102493). N.W.S. is grateful to The University of Queensland (UQ) for a PhD scholarship.
Abstract
The fluorine-directing effect has so far been exploited to provide short and efficient synthetic routes to rare l-ido sugars. However, the importance of anomeric configuration to its success has remained experimentally unverified. We now report on the synthesis of α- and β-configured per-O-benzoylated mannopyranosyl fluorides and initially show that their reactivity towards photo-bromination is strongly dependent on the anomeric configuration. The stereochemical basis of the fluorine-directing effect is then validated by revealing the striking difference in stereoselectivity observed for the free-radical reductions of the isolated 5-C-bromo sugars. This work importantly provides a synthetic route to a donor-functionalised derivative of l-gulose and reveals new insights into the behaviour of glycosyl radicals.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2149-4586.
- Supporting Information
Publikationsverlauf
Eingereicht: 10. Juli 2023
Angenommen nach Revision: 07. August 2023
Accepted Manuscript online:
07. August 2023
Artikel online veröffentlicht:
14. September 2023
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