1075748-91-2Relevant 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.
Oxidative heck reaction of glycals and aryl hydrazines: A palladium-catalyzed C-glycosylation
Bai, Yaguang,Kim, Le Mai Hoang,Liao, Hongze,Liu, Xue-Wei
supporting information, p. 8821 - 8825 (2013/09/24)
An efficient Heck-type C-glycosylation of glycals via the C-N bond cleavage of aryl hydrazines has been developed. The flexibility of the reaction was tested by the substrate scope, consisting of glycals from different carbohydrate origins as well as aryl hydrazines with various substituents. Pure α-C-glycosides were obtained when (3R)-glycals were employed, whereas α,β mixtures were observed with (3S)-glycals.
Efficient synthesis of rare sugar D-allal via reversal of diastereoselection in the reduction of protected 1,5-anhydrohex-1-en-3-uloses: Protecting group dependence of the stereoselection
Fujiwara, Takashi,Hayashi, Masahiko
supporting information; experimental part, p. 9161 - 9163 (2009/04/04)
(Chemical Equation Presented) D-Allal was selectively obtained by reducing bulky-silyl-protected 1,5-anhydrohex-1-en-3-uloses using the NaBH4 - CeCl3·7H2O system. The crucial point of this synthesis is the nature of the pr
