期刊
CURRENT TOPICS IN MEDICINAL CHEMISTRY
卷 3, 期 5, 页码 485-511出版社
BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/1568026033452429
关键词
-
Recent iminosugar syntheses starting both from commercially available sugars and non-glycidic precursors, are reported in this article. Exploiting carbohydrate starting materials, different synthetic approaches are described, mainly based on the introduction of an amino function in the sugar skeleton and the subsequent aminocyclization in order to generate the piperidine or pyrrolidine ring. The aminocyclization has been performed in different ways: reductive amination of azidoketones, intramolecular amino group attack on leaving groups and activated double bonds. In some cases one-pot amination and cyclization have been performed using ammonia or a primary amine and a di-functionalised sugar. Bicyclic compounds have also been obtained through these procedures. Starting from non-carbohydrate precursors, the nitrogen containing cycle, already present or easily obtained by Diels-Alder reactions, has been variously functionalised and stereo-differentiated by asymmetric induction or by resolution of the racemate. The syntheses of a variety of innovative structures, such as 1-N-iminosugars, iminosugars with two nitrogen atoms in the ring, iminosugars incorporating a guanidine function, imidazole-, triazole-and tetrazole-fused iminosugars, sugar-like aza-, oxa-, and thio-indolizidines, are reported. Finally the synthesis of glycoconjugate-related iminosugars, where the pseudoanomeric centre is linked to amino acid or peptide residues, and iminosugar phosphonates and nucleosides have been reviewed.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据