New approaches to synthetic receptors. Studies on the synthesis and properties of macrocyclic C-glycosyl compounds as chiral, water-soluble cyclophanes.
In an approach for the preparation of macrocyclic C-glycosyl compounds, the C-glycosyl residue is synthesized by acid-assisted reduction of a cyclic hemiacetal with sodium cyanoborohydride. Macrocycle formation is effected by the reaction of a symmetrical bis(C-glycosyl)derived diamine with a dicarboxylic acid dichloride. The product macrocycles are presented as the first examples of a new type of chiral, water-soluble cyclophane. Molecules of this type are of interest as synthetic receptors for lipophilic substrates.
Department of Chemistry, University of Texas at Austin 78712.
C S
CS
Wilcox
M D
MD
Cowart
D000475:Alkenes; D001952:Bridged-Ring Compounds; D002236:Carbohydrate Conformation; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009904:Optical Rotation; D013329:Structure-Activity Relationship
D000475:Alkenes; D001952:Bridged-Ring Compounds; D006027:Glycosides; D007202:Indicators and Reagents