Preparation of Regioselectively Modified Amylose Derivatives and Their Applications in Chiral HPLC

Sun, Bai-Shen; Li, Xiaofang; Zhong, Jun; Tian, Lili; Wang, Fang; Liu, Guihua; Tang, Shouwan; Pan, Fan

doi:10.1007/s10337-012-2338-x

Cited by 8 publications

(15 citation statements)

References 17 publications

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“…Finally, the 6‐hydroxyl group was regenerated by the removal of the trityl group in a methanol/HCl mixture and reacted with R 2 NCO to form the corresponding carbamate. It should be pointed out that in this study triphenylmethyl chloride was used instead of 4‐methoxytriphenylmethyl chloride to selectively protect the 6‐hydroxyl group and both of them were effective to protect the 6‐hydroxyl group as trityl ether …”

Section: Resultsmentioning

confidence: 97%

“…Investigations indicated that the substituent at 3‐position has a large influence on chiral recognition of regioselectively substituted amylose derivatives, which is also the same in this study. Bearing the same substituents at 2‐ and 6‐positions, 1b , 1d and 1h , 1a and 1f , and 1e and 1g , demonstrated changed chiral recognition relying on the substituent at 3‐position.…”

Section: Resultsmentioning

confidence: 99%

“…Especially racemates 3 and 5 were realized on 1e (α: 3 , 1.33; 5 , 1.08) rather than on 1f . These results implied that, as well as the substituent at 2‐position, the substituents at 3‐ and 6‐positions have a large influence on enantioseparation …”

Section: Resultsmentioning

confidence: 99%

“…In 2010, the Okamoto group extended the above work by synthesizing a series of amylose 2‐(substituted benzoate) derivatives and found that amylose 2‐(4‐ tert ‐butylbenzoate) and amylose 2‐(4‐chlorobenzoate) series showed high enantioseparation abilities . In 2012, Tang and coworkers prepared four novel regioselectively amylose derivatives bearing a chiral substituent, (S)‐1‐phenylethylcarbamate at 3‐ or 6‐position, and found that increased enantioselectivity could be achieved by introducing a chiral substituent at the 6‐achiral rather than the 3‐chiral position . Among the derivatives, amylose 2‐benzoate‐3‐(3,5‐dimethylphenylcarbamate/3,5‐dichlorophenylcarbamate)‐6‐((S)‐1‐phenylethylcarbamate) exhibited chiral recognition abilities comparable to that of Chiralpak AD .…”

Section: Introductionmentioning

confidence: 99%

“…In 2012, Tang and coworkers prepared four novel regioselectively amylose derivatives bearing a chiral substituent, (S)‐1‐phenylethylcarbamate at 3‐ or 6‐position, and found that increased enantioselectivity could be achieved by introducing a chiral substituent at the 6‐achiral rather than the 3‐chiral position . Among the derivatives, amylose 2‐benzoate‐3‐(3,5‐dimethylphenylcarbamate/3,5‐dichlorophenylcarbamate)‐6‐((S)‐1‐phenylethylcarbamate) exhibited chiral recognition abilities comparable to that of Chiralpak AD . Recently, the regioselective introduction of substituents at 2‐, 6‐positions and 3‐postion have been carried out through the regioselective protection at 2‐ and 6‐positions using a bulky trialkylsilyl chloride …”

Section: Introductionmentioning

confidence: 99%

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Preparation and evaluation of regioselectively substituted amylose derivatives for chiral separations

et al. 2017

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Six novel regioselectively substituted amylose derivatives with a benzoate at 2-position and two different phenylcarbamates at 3- and 6-positions were synthesized and their structures were characterized by H nuclear magnetic resonance (NMR) spectroscopy. Their enantioseparation abilities were then examined as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) after they were coated on 3-aminopropyl silica gels. Investigations indicated that the substituents at the 3- and 6-positions played an important role in chiral recognition of these amylose 2-benzoate serial derivatives. The derivatives demonstrated characteristic enantioseparation and some racemates were better resolved on these derivatives than on Chiralpak AD, which is one of the most efficient CSPs, utilizing coated amylose tris(3,5-dimethylphenylcarbamate) as the chiral selector. Among the derivatives prepared, amylose 2-benzoate-3-(phenylcarbamate/4-methylphenylcarbamate)-6-(3,5-dimethylphenylcarbamate) exhibited chiral recognition abilities comparable to that of Chiralpak AD and may be useful CSPs in the future. The effect of mobile phase on chiral recognition was also studied. In general, with the decreased concentration of 2-propanol, better resolutions were obtained with longer retention times. Moreover, when ethanol was used instead of 2-propanol, poorer resolutions were often achieved. However, in some cases, improved enantioselectivity was achieved with ethanol rather than 2-propanol as the mobile phase modifier.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Preparation and evaluation of regioselectively substituted amylose derivatives for chiral separations

et al. 2017

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Enantiomer separation on novel cellulose derivatives bearing regioselective phenylcarbamate groups

Tang

Wang

Yan

et al. 2020

J of Separation Science

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Four novel regioselectively carbamoylated cellulose derivatives with two types of substituents, one being a 3‐chloro‐4‐methylphenylcarbamate group and the other being a phenylcarbamate, a 3,5‐dichlorophenylcarbamate or a 4‐methylphenylcarbamate group, at the 2‐, 3‐positions and 6‐position were synthesized and utilized as chiral stationary phases in high‐performance liquid chromatography. The obtained derivatives exhibited characteristic chiral recognition abilities which were significantly affected by the nature and arrangement of the groups at the 2‐, 3‐positions and 6‐position. Compared with cellulose tris(3‐chloro‐4‐methylphenylcarbamate) and Chiralcel OD columns, several racemates were better resolved on these new phases. With all six racemates resolved on cellulose 2,3‐bis(4‐methylphenylcarbamate)‐6‐(3‐chloro‐4‐methylphenylcarbamate), it appears to be a potential useful chiral stationary phase in the future. Also, the influence of mobile phase on chiral recognition was investigated. Better resolutions were generally obtained with decreased amount of 2‐propanol with a mixture of hexane/2‐propanol as the mobile phase. Moreover, when ethanol was used instead of 2‐propanol as the mobile phase modifier, poorer enantioseparations were often achieved.

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Regioselectively substituted cellulose mixed esters synthesized by two-steps route to understand chiral recognition mechanism and fabricate high-performance chiral stationary phases

Yin

Zhang

Chang

et al. 2019

Analytica Chimica Acta

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Preparation of Regioselectively Modified Amylose Derivatives and Their Applications in Chiral HPLC

Cited by 8 publications

References 17 publications

Preparation and evaluation of regioselectively substituted amylose derivatives for chiral separations

Preparation and evaluation of regioselectively substituted amylose derivatives for chiral separations

Enantiomer separation on novel cellulose derivatives bearing regioselective phenylcarbamate groups

Regioselectively substituted cellulose mixed esters synthesized by two-steps route to understand chiral recognition mechanism and fabricate high-performance chiral stationary phases

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