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Số người truy cập: 107,110,107

 Synthesis and Chiral Recognition Ability of Cellulose-Based Chiral Selectors with Regioselective Substituents Obtained by Carbonate Aminolysis
Tác giả hoặc Nhóm tác giả: Bui, C. V.; Frühauf, P.; Lindner, W.; Thomas, R.; Hettegger, H.
Nơi đăng: 16th European Workshop on Lignocellulosics and Pulp; Số: June 28th – July 1st;Từ->đến trang: Gothenburg, Sweden.;Năm: 2022
Lĩnh vực: Khoa học công nghệ; Loại: Báo cáo; Thể loại: Quốc tế
TÓM TẮT
A regioselective pathway for the controlled synthesis of novel cellulose 2,3-bis(3,5-dimethylphenyl carbamate)-6-(α-phenylethyl carbamate) chiral selectors combining both isocyanate and oxycarbonylation/aminolysis reactions is presented. The selective reaction of phenyl chloroformate towards C6-OH of cellulose was comprehensively investigated and evaluated. The intermediate was subsequently allowed to react with 3,5-dimethylphenyl isocyanate to obtain cellulose 2,3-bis(3,5-dimethylphenyl carbamate)-6-(phenyl carbonate). Aminolysis of the reactive carbonate moiety with enantiopure (R)- or (S)-α-phenylethylamine yielded the respective regioselectively modified novel chiral selectors. The cellulose derivatives were comprehensively characterized by ATR-FTIR, solid-state 13C NMR, GPC, and elemental analysis. With the optimized synthesis protocols in hand, it was possible to overcome shortcomings of previous protocols for the preparation of chiral stationary phases bearing different carbamate moieties at 2,3- and 6-positions, and to obtain carbamate structures beyond the standard functionalities accessible through isocyanate reagents using simple and commercially available primary amine reagents instead. The enantioseparation efficiency of the novel cellulose-derivative-based chiral selectors was evaluated and compared to cellulose tris(3,5-dimethylphenyl carbamate) as a reference chiral selector prepared with the same coating amount, coating process, silica gel materials, and HPLC conditions.
ABSTRACT
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