1607468-98-3Relevant academic research and scientific papers
ring opening-ring closure strategy for the synthesis of aryl-C-glycosides
Liu, Chen-Fu,Xiong, De-Cai,Ye, Xin-Shan
, p. 4676 - 4686 (2014)
A new ring-opening-ring closure strategy for the synthesis of aryl-C-glycosides was described. This strategy exploited the nickel-catalyzed regioselective β-O elimination of glycals by reactions with various aryl boronic acids or potassium aryltrifluoroborates to yield the ring-opened products, which underwent the Lewis acid, protonic acid, PhSeCl, or NBS mediated ring closure reactions to afford diverse aryl-C-glycosides. After Lewis acids and protonic acids were screened, it was found that, starting from the ring-opened substrates, the Ph3PHBr or Sc(OTf)3 mediated ring closure reaction provided α- or β-preferred aryl-C- Δ2,3-glycosides, respectively. Furthermore, β-d-phenyl-C-glycosides were successfully prepared via the PhSeCl-mediated cyclization reaction, whereas the α-d-phenyl-C-glycoside was obtained via the NBS-mediated cyclization reaction. After removal of the 2-substituted functionalities by Bu3SnH/AIBN, the synthesis of 2-deoxy-aryl-C- glycosides was ultimately realized in a stereoselective manner.
