Radicamine A was prepared via a key intermediate-cycle nitrone 5 by using D-arabinose as the raw material with a total yield of 15.5%.Cycle nitrone 5 was synthesized by protection of hydroxyl group,introduction of nit...Radicamine A was prepared via a key intermediate-cycle nitrone 5 by using D-arabinose as the raw material with a total yield of 15.5%.Cycle nitrone 5 was synthesized by protection of hydroxyl group,introduction of nitrogen and intromolecular cyclization.And then it had a high stereoselective addition reaction with aryl Grignard reagents 6 to form compound 7.Finally,the target compound was obtained by catalytic hydrogenation of compound 7.The novel compounds 3 and 4 were confirmed by 1HNMR,IR,MS and elemental analysis.展开更多
Three pairs of novel 2-aryl-3,4,5-trihydroxypiperidines （6-8 and their enantiomers）, the piperidine analogues of the pyrrolidine alkaloids radicamine A and radicamine B, were prepared from six- membered cyclic nitro...Three pairs of novel 2-aryl-3,4,5-trihydroxypiperidines （6-8 and their enantiomers）, the piperidine analogues of the pyrrolidine alkaloids radicamine A and radicamine B, were prepared from six- membered cyclic nitrones through a concise two-step procedure, i.e., Grignard reagent addition and deprotection. These novel polyhydroxylated piperidine iminosugars were assayed against 10 types of enzymes. Only compound 8 exhibited weak inhibition （IC50 1080 μmol/L） against β-galactosidase from rat intestinal lactases.展开更多
文摘Radicamine A was prepared via a key intermediate-cycle nitrone 5 by using D-arabinose as the raw material with a total yield of 15.5%.Cycle nitrone 5 was synthesized by protection of hydroxyl group,introduction of nitrogen and intromolecular cyclization.And then it had a high stereoselective addition reaction with aryl Grignard reagents 6 to form compound 7.Finally,the target compound was obtained by catalytic hydrogenation of compound 7.The novel compounds 3 and 4 were confirmed by 1HNMR,IR,MS and elemental analysis.
基金Financial support from National Basic Research Program of China (Nos. 2012CB822101 and 2011CB808603)the Natural Science Foundation of China (Nos. 21272240 and 21102149)
文摘Three pairs of novel 2-aryl-3,4,5-trihydroxypiperidines （6-8 and their enantiomers）, the piperidine analogues of the pyrrolidine alkaloids radicamine A and radicamine B, were prepared from six- membered cyclic nitrones through a concise two-step procedure, i.e., Grignard reagent addition and deprotection. These novel polyhydroxylated piperidine iminosugars were assayed against 10 types of enzymes. Only compound 8 exhibited weak inhibition （IC50 1080 μmol/L） against β-galactosidase from rat intestinal lactases.
