Reagent-Controlled Divergent Synthesis of <i>C</i>-Glycosides
Puren Han, Jianchao Liu, Jin‐Xi Liao, Yuan‐Hong Tu, Jiansong Sun
Abstract
By turning on or switching off the directing effect of the C3–OH-located o-diphenylphosphanylbenzoyl (o-DPPB) group in glycals, a reagent-controlled protocol for divergent and regio- and stereoselective syntheses of C-glycosides has been established. In particular, the silence of the directing effect of o-DPPB was achieved by the introduction of a ZnCl2 additive, which is operationally simple and efficient. The flexibility of the novel protocol was exhibited not only by the easy access of both α- and β-C-glycosides but also by the versatility of the obtained formal Ferrier rearrangement products, which can be easily derivatized to various C-glycoside analogues owing to the embedded multifunctionalities.