221658-15-7Relevant academic research and scientific papers
Development of Routes for the Stereoselective Preparation of β-Aryl- C-glycosides via C-1 Aryl Enones
Kanaujiya, Vimlesh Kumar,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Singh, Adesh Kumar,Tiwari, Varsha
, p. 7650 - 7655 (2020)
A wide range of enones derived from d-glucal, d-galactal, l-rhamnal, d-rhamnal, and l-arabinal underwent Heck-coupling with various arylboronic acids bearing electron-donating and -withdrawing groups in the presence of palladium acetate and 1,10-phenanthroline. These reactions provided synthetically useful C-1 aryl enones in good yields. Many sensitive functional groups as well as protecting groups present in arylboronic acids and enones, respectively, remained intact under optimized conditions. The stereoselective hydrogenation of C-1 aryl enones with Pd-C/H2 provides the β-isomer of 2-deoxy-aryl-C-glycosides in excellent yield. The C-1 aryl enones were also used as precursors for the synthesis of 2-hydroxy-β-aryl-C-glycosides. Regioselective C-2 halogenations and vinylations of C-1 aryl enones were achieved in excellent yields.
Simple oxidation of 3-O-silylated glycals: Application in deblocking 3-0-protected glycals
Kirschning, Andreas,Hary, Ulrike,Plumeier, Claus,Ries, Monika,Rose, Lars
, p. 519 - 528 (2007/10/03)
A high yielding allylic oxidation of 3-O-siIylated glycals 5-10 with the reagent system PhI(OAc)2-TMSN3 is presented. The iodine(m) species generated under these conditions is a lot more effective for generating carbohydrate-derived 3-trialkylsiloxy-2,3-d
