1020168-41-5Relevant academic research and scientific papers
Cerium(IV)-mediated C-C bond formations in carbohydrate chemistry
Elamparuthi, Elangovan,Kim, Boo Geun,Yin, Jian,Maurer, Michael,Linker, Torsten
experimental part, p. 11925 - 11937 (2009/04/07)
We provide a comprehensive study on the addition of radicals to unsaturated carbohydrates in the presence of cerium(IV) ammonium nitrate (CAN). The method is applicable to hexoses, pentoses, and disaccharides, tolerates different protecting groups, and is characterized by mild reaction conditions. Best substrates are malonates and glycals, which afford 2-C-branched carbohydrates in high yields and stereoselectivities. For the first time, the anomeric radicals were trapped with nucleophiles after oxidation and thus the 1- and 2-position of glucose were functionalized in one step. Nitro compounds are suitable CH acidic radical precursors as well, offering an easy access to C-analogs of glycosamines in moderate to good yields. Finally, selective reductions demonstrate the synthetic potential of cerium(IV)-mediated radical reactions in carbohydrate chemistry.
Convenient synthesis of branched-chain glycosamines by radical addition of nitromethane to glycals
Elamparuthi, Elangovan,Linker, Torsten
supporting information; experimental part, p. 1361 - 1364 (2009/04/10)
(Chemical Equation Presented) Radical addition-reduction-acetylation is the simple three-step sequence for the synthesis of branched-chain glycosamines 3 from glycals 1 and nitromethane (2). The intermediary formed 2-C-nitromethyl-pyranosides are valuable
