Generation of Glycosyl Radicals from Glycosyl Sulfoxides and Its Use in the Synthesis of<i>C</i>‐linked Glycoconjugates
Weidong Shang, Shengnan Su, Rong Shi, Ze‐Dong Mou, YU Guo-qiang, Xia Zhang, Dawen Niu
Abstract
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.
Topics & Concepts
GlycosylChemistryGlycoconjugateRadicalIntramolecular forceMoietyIodideCombinatorial chemistryArylOrganic chemistryAlkylBiochemistryRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCarbohydrate Chemistry and Synthesis