Synthesis of regioselectively substituted cellulose derivatives and applications in chiral chromatography

✍ Scribed by Murat Acemoglu; Ernst Küsters; Jürgen Baumann; Ivan Hernandez; Ching Pong Mak

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 349 KB
• Volume: 10
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1998)10:4<294::aid-chir3>3.0.co;2-8

✦ Synopsis

Various cellulose-2,3-bis-arylcarbamate-6-O-arylesters and cellulose-2,3bis-arylester-6-O-arylcarbamates, designed to test the possible combined effects of the known tris-arylcarbamate and tris-arylester classes, were synthesized with high regioselectivity at O-C( 6), and their use as CSPs in liquid chromatography for enantiomeric separations was investigated. The separations obtained with the synthesized CSPs were compared to the separations achieved on a self-packed reference column, consisting of cellulose-tris-(3,5-dimethylphenyl-carbamate) as CSP standard. Among the synthesized, regioselectively substituted cellulose derivatives, 2,3-bis-O-(3,5-dimethylphenylcarbamate)-6-O-benzoate-cellulose and 2,3-bis-O-(benzoate)-6-O-(3,5-dichlorophenylcarbamate)-cellulose gave the best CSPs for the separation of the test racemates. CSPs from regioselectively substituted cellulose derivatives seem to exhibit higher selectivities than cellulose-tris-(3,5-dimethylphenylcarbamate) for certain classes of racemic compounds.