1403609-08-4Relevant 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
supporting information, p. 7650 - 7655 (2020/10/09)
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.
Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization
Yalamanchili, Subbarao,Miller, William,Chen, Xizhao,Bennett, Clay S.
supporting information, p. 9646 - 9651 (2019/12/02)
A flexible de novo route capable of producing libraries of 2,6-dideoxy sugars is described. We have found that Au(JackiePhos)SbF6MeCN promotes the conversion of homopropargyl orthoesters into functionalized 2,3-dihydro-4H-pyran-4-ones in good t
