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Conformation of Glycosyl Radicals: Radical Stabilization by β‐CO Bonds
Abstract
A transformation from the chair- into the boat conformation takes place when glucosides such as 1 are converted into glucosyl radicals 2. This preference for the boat conformation is due to the radical-stabilizing effect of the coplanar arrangement of the β-CO bond and semi-occupied orbital. The findings are of interest regarding stereoselective radical CC-linkage in the synthesis of C-glycosides.
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Citations
Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Thiyl Radicals in Organic Synthesis
Dénès, F., Pichowicz, M., Povie, G., & Renaud, P. (2014) · Chemical Reviews · doi:10.1021/cr400441m · Cited by 985
Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light
Andrews, R. S., Becker, J. J., & Gagné, M. R. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201004311 · Cited by 300
Metadata
- Authors
- Dupuis, J., Giese, B., Rüegge, D., Fischer, H., Korth, H., & Sustmann, R.
- Venue
- Angewandte Chemie International Edition in English
- Publisher
- Wiley
- Published
- 1984-11
- Volume
- 23
- Issue
- 11
- Pages
- 896-898
- ISSN
- 0570-0833 (ISSN-L)
- OpenAlex
- W2034469225
- Cited by
- 183
- References
- 0
- FWCI
- 5.56
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Conformation of Glycosyl Radicals: Radical Stabilization by β‐CO Bonds. https://app.cochat.ai/papers/10.1002/anie.198408961
- The paper
- Dupuis, J., Giese, B., Rüegge, D., Fischer, H., Korth, H., & Sustmann, R. (1984). Conformation of Glycosyl Radicals: Radical Stabilization by β‐CO Bonds. Angewandte Chemie International Edition in English. https://doi.org/10.1002/anie.198408961
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
