Tautomeric rearrangement of 3-deoxy-3-thioureidoaldoses: a novel synthetic route to carbohydrate mimics having a cyclic thiourea structure

Abstract
Cyclic thiourea glycomimetics structualy related to 3-deoxyy-2-nonulosonic acid (KDNs) and 1,5-dideoxy-1,5-iminooctitols (azaoctitols) have been prepared by tautomeric rearrangement of 3-decoy-3-thioureidoaldohexoses; the conformational properties of these compounds are governed by stereoelectronic requirements, mainly the anomeric effect.