Y. Mai-Linde, T. Linker
Radical Clock Probes to Determine Carbohydrate Radical Stabilities
Org. Lett. 2020, 22, 1525–1529
DOI: 10.1021/acs.orglett.0c00111
Carbohydrate radical stabilities in the 1- and 2-position have been determined by a radical clock approach, starting from cyclopropanated sugars with xanthate 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.
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