Weidong Shang; Sheng-Nan Su; Rong Shi; Ze-Dong Mou; Guo-Qiang Yu,; Xia Zhang; Dawen Niu
Angew. Chem. Int. Ed. Engl., 2021, 60(1), 385-390
https://doi.org/10.1002/anie.202009828

Abstract

We here report glycosyl sulfoxides appended with an aryl iodide moiety as readily available, air and moisture stable precursors to glycosyl radicals. These glycosyl sulfoxides could be converted to glycosyl radicals by way of a rapid and efficient intramolecular radical substitution event. The use of this type of precursors enabled the synthesis of various complex C-linked glycoconjugates under mild conditions. This reaction could be performed in aqueous media and is amenable to the synthesis of glycopeptidomimetics and carbohydrate-DNA conjugates.