Radical clock probes to determine carbohydrate radical stabilities
- Carbohydrate radical stabilities in the 1- and 2-position have been determined by a radical clock approach, starting from cyclopropanated sugars with xanthates as precursors. Various hexoses and pentoses afforded 1-deoxy sugars as main products, indicating that anomeric radicals are more stable than radicals in the 2-position. An additional influence of the configurations on radical stabilities has been observed. Our results should be interesting for the understanding of 1,2-radical rearrangements in carbohydrate chemistry and offer an easy access to deoxy-vinyl sugars.
| Author details: | Yasemin Mai-LindeORCiD, Torsten LinkerORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1021/acs.orglett.0c00111 |
| ISSN: | 1523-7060 |
| ISSN: | 1523-7052 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/32009406 |
| Title of parent work (English): | Organic letters |
| Publisher: | American Chemical Society |
| Place of publishing: | Washington |
| Publication type: | Article |
| Language: | English |
| Date of first publication: | 2020/02/03 |
| Publication year: | 2020 |
| Release date: | 2022/11/25 |
| Tag: | beta-(acyloxy)alkylrear; chemistry; convenient synthesis; cyclopropanation; glycals; mechanism; rangement; stereoselective-synthesis; sugars |
| Volume: | 22 |
| Issue: | 4 |
| Number of pages: | 5 |
| First page: | 1525 |
| Last Page: | 1529 |
| Funding institution: | University of Potsdam |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
