Synthesis of polysaccharide derivatives bearing bromobenzoate pendants for use as chiral auxiliaries

Ikai, Tomoyuki; Kimura, Kazuma; Maeda, Katsuhiro; Kanoh, Shigeyoshi

doi:10.1016/j.reactfunctpolym.2014.06.001

Cited by 8 publications

(3 citation statements)

References 56 publications

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“…Cellulose is an abundant carbohydrate-based resource on earth and is also optically active. 33,34 The cellulose-based chiral materials for both resolution and asymmetric synthesis often show better performances than the corresponding glucosebased materials, suggesting the importance of the helical chirality derived from the cellulose backbone rather than the central chirality in the repeating glucose units. 31,32 Today, cellulose-based CSPs are widely used not only for microanalyses of enantiomer compositions, but also for large-scale preparation of pure enantiomers.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, we reported purpose-designed cellulose derivatives bearing catalytically active sites and reactive prochiral units as pendant groups, which can be used as asymmetric catalysts and chiral auxiliaries for asymmetric syntheses, respectively. 33,34 The cellulose-based chiral materials for both resolution and asymmetric synthesis often show better performances than the corresponding glucosebased materials, suggesting the importance of the helical chirality derived from the cellulose backbone rather than the central chirality in the repeating glucose units.…”

Section: Introductionmentioning

confidence: 99%

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Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

et al. 2016

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Chiral fluorescent sensors were designed and synthesized from naturally occurring optically active cellulose, in which a terthienyl moiety was used as a fluorescent signaling unit, and their chiral recognition abilities were investigated on the basis of an enantioselective fluorescence response to aromatic nitro compounds as quenchers. A cellulose phenylcarbamate derivative (Ce-1b) exhibited an apparent enantioselectivity for various types of aromatic nitro compounds containing either central or axial chirality. Considering the fact that a corresponding monosaccharide derivative showed almost no enantioselectivity, the chiral recognition ability of the cellulose-based fluorescence sensor is attributed to its regular higherorder structures, probably a one-handed helical conformation. The resolution ability of Ce-1b as a chiral stationary phase for high-performance liquid chromatography was basically higher than that of the previously reported cellulose tris( phenylcarbamate), revealing that the terthienyl-based pendant provides attractive chiral recognition sites along the helical backbone as well as the fluorescent functionality. † Electronic supplementary information (ESI) available. See

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

et al. 2016

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“…Although great success has been achieved in the application of polysaccharide derivatives in CSP materials, their application in other fields of chiral materials has been highly restricted. We have reported functionalized polysaccharide derivatives bearing reactive prochiral units or catalytically active sites as pendant groups with the aim of developing chiral auxiliaries or asymmetric catalysts, respectively, for asymmetric synthesis [11,12]. In addition, a cellulose-based chiral fluorescent sensor (Ce- 1b in Figure 1) containing a terthienyl moiety as a fluorescent signaling unit has also been developed and was found to show apparent enantioselectivity for various types of chiral compounds containing either central or axial chirality [13].…”

Section: Introductionmentioning

confidence: 99%

Development of Amylose- and β-Cyclodextrin-Based Chiral Fluorescent Sensors Bearing Terthienyl Pendants

et al. 2016

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Phenylcarbamate derivatives of amylose and β-cyclodextrin show excellent chiral recognition when used as chiral stationary phases (CSPs) for high-performance liquid chromatography. To open up new possibilities of carbohydrate-based materials, we developed chiral fluorescent sensors based on amylose and β-cyclodextrin (Am-1b and CyD-1b, respectively) by attaching fluorescent π-conjugated units on their side chains. Their recognition abilities toward chiral analytes containing a nitrophenyl unit were evaluated by measuring the enantioselective fluorescence quenching behavior. Both sensors showed the same degree of enantioselective fluorescence response for various aromatic nitro compounds. However, in some cases, their enantioselectivities were different depending on the analytes. The difference in the chiral recognition abilities between Am-1b and CyD-1b seems to be based on the structural difference of their inherent backbones, that is, the one-handed helical structure and cyclic structure, respectively. The study on the resolution ability of the Am-1b-based CSP revealed that the terthienyl-based pendant of Am-1b provides not only a fluorescent functionality but also a different chiral recognition site from that of amylose tris(phenylcarbamate).

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Methods and Principles of Functionalization

2019

Functional Synthetic Polymers

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Synthesis of polysaccharide derivatives bearing bromobenzoate pendants for use as chiral auxiliaries

Cited by 8 publications

References 56 publications

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

Development of Amylose- and β-Cyclodextrin-Based Chiral Fluorescent Sensors Bearing Terthienyl Pendants

Methods and Principles of Functionalization

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