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Số người truy cập: 112,298,152

 Optimization of the regioselective synthesis of mixed cellulose 3,5‑dimethylphenyl and α‑phenylethyl carbamate selectors as separation phases for chiral HPLC
Tác giả hoặc Nhóm tác giả: Cuong Viet Bui, Thomas Rosenau, and Hubert Hettegger
Nơi đăng: Cellulose; Số: Online;Từ->đến trang: 1-15;Năm: 2023
Lĩnh vực: Khoa học công nghệ; Loại: Bài báo khoa học; Thể loại: Quốc tế
TÓM TẮT
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 and optimized the critical aspects of regioselective tritylation and detritylation at C6 of the glucopyranose units of the polysaccharide backbone. The advantage of using cellulose II in comparison to cellulose I for tritylation was analyzed and the detritylation time was determined by a fast and simple thin-layer chromatography method. Optimization of both tritylation and detritylation was accompanied by a combination of analytical techniques.
Oxycarbonylation with phenyl chloroformate was used to introduce a reactive phenyl carbonate moiety at C6 of the intermediate cellulose 2,3-bis(3,5-dimethylphenyl carbamate), which was subsequently converted to the respective cellulose 6-(α-phenylethyl carbamate) derivative by aminolysis with enantiopure (R)- or (S)-α-phenylethylamine. The starting material, intermediates, and target cellulose derivatives were comprehensively analytically characterized by ATR-FTIR, solid- and liquid-state 13C NMR, GPC, and elemental analysis. With the optimized protocol,
it became possible to obtain cellulose carbamate-type chiral selectors through carbonate aminolysis with simple and commercially available primary amines instead of reaction with isocyanate reagents. The enantioseparation performance of the obtained chiral selectors was evaluated against cellulose tris(3,5-dimethylphenyl carbamate) as a reference selector
with a selection of chiral analytes.
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 and optimized the critical aspects of regioselective tritylation and detritylation at C6 of the glucopyranose units of the polysaccharide backbone. The advantage of using cellulose II in comparison to cellulose I for tritylation was analyzed and the detritylation time was determined by a fast and simple thin-layer chromatography method. Optimization of both tritylation and detritylation was accompanied by a combination of analytical techniques.
Oxycarbonylation with phenyl chloroformate was used to introduce a reactive phenyl carbonate moiety at C6 of the intermediate cellulose 2,3-bis(3,5-dimethylphenyl carbamate), which was subsequently converted to the respective cellulose 6-(α-phenylethyl carbamate) derivative by aminolysis with enantiopure (R)- or (S)-α-phenylethylamine. The starting material, intermediates, and target cellulose derivatives were comprehensively analytically characterized by ATR-FTIR, solid- and liquid-state 13C NMR, GPC, and elemental analysis. With the optimized protocol,
it became possible to obtain cellulose carbamate-type chiral selectors through carbonate aminolysis with simple and commercially available primary amines instead of reaction with isocyanate reagents. The enantioseparation performance of the obtained chiral selectors was evaluated against cellulose tris(3,5-dimethylphenyl carbamate) as a reference selector
with a selection of chiral analytes.
[ 2023\2023m01d04_20_36_19Paper_5.pdf ]
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