1020168-31-3Relevant academic research and scientific papers
Sugar amino acids and oligosaccharide mimic prepared from sugar amino acids
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Paragraph 0052; 0054; 0059, (2018/10/04)
Belonging to the field of carbohydrate chemistry, the invention in particular relates to sugar amino acids and an oligosaccharide mimic prepared from the same. Cheap and easily available D-glucose andD-galactose are adopted as the starting raw materials for a series of reactions to obtain all-benzyl-protected glycal, the latter undergoes one-step free radical addition under the action of ceric ammonium nitrate (CAN) to obtain a precursor 2-C-nitro compound of SAAs, then Pd/C hydrogenation reaction for deprotection of Bn, reductive ammoniation and selective Boc protection reaction are carriedout to obtain a protected intermediate product of amino; then TIPSCl is utilized for selective protection of C-6 hydroxyl, then C-3 hydroxyl and C-4 hydroxyl are subjected to Bn protection, and deprotection of TIPS is carried out on C-6 hydroxyl; finally the C-6 hydroxyl is oxidized to obtain glucose-type and galactose-type SAAs blocks; and based on the obtained SAAs, a straight-chain type oligosaccharide mimic connected by an amido bond is synthesized, and condensation reaction is carried out to obtain 9 homologous and heterologous oligosaccharide mimics of straight-chain dimer, tetramer andoctamer. The method is simple, convenient, fast and effective.
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
