Stereoselective syntheses of polyhydroxylated azepane derivatives from sugar-based epoxyamides. Part 1: synthesis from D-mannose
An approach to the synthesis of polyhydroxyazepane derivatives from sugar-based epoxyamides or epoxyalcohols, in which the total regioselective epoxide opening by nitrogen nucleophiles is the key step, is described. Thus, novel polyhydroxyazepane carboxamides and aminomethyl polyhydroxyazepanes, with potential pharmacological interest, are synthesized from diacetone D-mannose. Configurational assignments of the obtained products were determined. (C) 2010 Elsevier Ltd. All rights reserved.
Keywords: Glycosidase Inhibitory-Activities ; Stabilized Sulfur Ylides ; 7-Membered Iminocyclitols ; Mimicking Monosaccharides ; Iminosugar Derivatives ; Glucosidase Inhibitors ; Fucosidase Inhibitors ; Alpha-Glucosidase ; Beta-Glucosidase ; Discovery
Record created on 2011-12-16, modified on 2016-08-09