Optimization of the regioselective synthesis of mixed cellulose 3,5-dimethylphenyl and α-phenylethyl carbamate selectors as separation phases for chiral HPLC

Abstract Regioselective tritylation and carbonate aminolysis were employed in this work to synthesize cellulose 2,3- bis (3,5-dimethylphenyl carbamate)-6-( α -phenylethyl carbamate)-type chiral selectors. We evaluated optimized the critical aspects of regioselective detritylation at C6 glucopyranose units polysaccharide backbone. The advantage using II comparison I for was analyzed time determined by a fast simple thin-layer chromatography method. Optimization both accompanied combination analytical techniques. Oxycarbonylation with phenyl chloroformate used introduce reactive moiety intermediate carbamate), which subsequently converted respective 6-( carbamate) derivative enantiopure ( R )- or S -phenylethylamine. starting material, intermediates, target derivatives comprehensively analytically characterized ATR-FTIR, solid- liquid-state 13 C NMR, GPC, elemental analysis. With protocol, it became possible obtain carbamate-type selectors through commercially available primary amines instead reaction isocyanate reagents. enantioseparation performance obtained against tris as reference selector selection analytes. Graphical abstract