Synthesis and Characterization of Sugar-Based Chiral Ligands
Project no. 21386 · Status: Kapanmış · 2019
Summary
Firstly, the experimental works were constituted on the simple synthesis of the 6-amino derivatives of 1,2-O-(R)-trichloroethylidene-?-D-glucofuranose (?-chloralose)and 1,2-O-(S)-trichloroethylidene-?-D-galactofuranose in this study.The trichloroethylidene acetals of D-glucose and D-galactose was prepared from the reaction of sugars and anhydrous chloral. Tosyl derivates of trichloroethylidene acetals of D-glucose and D-galactose were obtained by reaction of these compounds with p-toluenesulfonylchloride and then, these tosyl derivates were converted to the azide form by following nuclephilic substitution reaction. Obtained azide derivates were reacted with triphenylphosphine as reducing agent in order to get the related amino-sugars derivates. Then, in order to synthesize chiral sugar based Schiff bases; the solution of aldehyde (salicylaldehyde or 3,5-ditbutylsalicylaldehyde) in EtOH was added dropwise into the solution of amino sugar derivative in EtOH solution in RT at the end of the reaction. The structures of all the compounds were determined by using spectroscopic techniques such as 1H-NMR, 13C-NMR and IR in this project. Keywords: Chloralose, Amino Sugar, Chiral Schiff Base, Asymmetric Synthesis.