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Preparation method and application of novel triazole bridging compound cyclodextrin chiral stationary phase

A chiral stationary phase, cyclodextrin technology, applied in chemical instruments and methods, other chemical processes, etc., can solve the problem of weakened enantiomeric resolution, weakened natural cyclodextrin hydroxyl hydrogen bonds, new bonding arms Development difficulties and other problems, to achieve the effect of improving separation performance and separation throughput, enhancing chiral recognition ability, and enriching structural design

Inactive Publication Date: 2013-12-25
TIANJIN UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] To sum up, the current research on cyclodextrin stationary phases at home and abroad is mainly focused on the single-layer cyclodextrin stationary phase based on functional bonded arms and new cyclodextrin derivatives, and great progress has been made. A series of excellent cyclodextrin stationary phases, but there are still many problems: First, the development of new bonded arms with multiple The arm has limited ability to improve the chiral recognition performance of the stationary phase; secondly, although the cyclodextrin modification group greatly improves its chiral selectivity by introducing π-π bonds, hydrogen bonds, hydrophobic interactions, and dipole interactions , expanding the application space, but different modified cyclodextrins can only split specific types of enantiomers, which is highly targeted; thirdly, cyclodextrin modification weakens the natural cyclodextrin while introducing three-dimensional interaction groups. Hydrogen bonding of dextrin hydroxyl groups leads to weakening or even disappearance of its ability to resolve some enantiomers

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  • Preparation method and application of novel triazole bridging compound cyclodextrin chiral stationary phase
  • Preparation method and application of novel triazole bridging compound cyclodextrin chiral stationary phase
  • Preparation method and application of novel triazole bridging compound cyclodextrin chiral stationary phase

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preparation example Construction

[0035] like figure 2 Shown, the preparation method of novel triazole bridged complex cyclodextrin chiral stationary phase of the present invention, the steps are as follows:

[0036] Step 1, the preparation of azide-containing monosubstituted cyclodextrin and alkynyl-containing monosubstituted cyclodextrin, including:

[0037] 1-1) Preparation of azide cyclodextrin: add mono-6-p-toluenesulfonyl cyclodextrin and sodium azide to water; the mono-6-p-toluenesulfonyl cyclodextrin used can be Mono-6-p-toluenesulfonyl-α-cyclodextrin, Mono-6-p-toluenesulfonyl-β-cyclodextrin and Mono-6-p-toluenesulfonyl-γ-cyclodextrin One of them, the molar ratio of mono-6-p-toluenesulfonyl cyclodextrin and sodium azide is 1:0.5~1:5, react at 55~110°C for 10~30 hours, and then The reaction system was poured into acetone to precipitate a solid, filtered, washed twice with acetone, and dried to obtain mono-6-azidocyclodextrin;

[0038] The structure of the resulting azide cyclodextrin can be expresse...

Embodiment 1

[0061] In a 50 mL three-necked flask under nitrogen protection, 16 mL of propargylamine was added, and then 6 g of mono-6-p-methylbenzenesulfonyl-β-cyclodextrin was added, and heated to reflux at 90° C. for 24 hours. After cooling to room temperature under nitrogen protection, the reaction system was poured into 90 mL of acetonitrile to precipitate a solid. The solid was washed twice with acetonitrile to obtain the product mono-6-deoxy-N-propargylamino-β-cyclodextrin.

[0062] Add 50 mL of distilled water into a 100 mL three-necked flask, then add 5 g of mono-6-p-methylbenzenesulfonyl-β-cyclodextrin, then add 1.26 g of sodium azide, and heat to 85° C. for 20 hours. The reaction system was poured into 250 mL of acetone to precipitate a solid. The solid was washed twice with acetone to obtain mono-6-deoxy-azido-β-cyclodextrin.

[0063] Add 50mL of anhydrous DMF to a 100mL three-necked flask, then add 1.74g of mono-6-deoxy-azido-β-cyclodextrin, then add 0.27g of sodium hydride ...

Embodiment 2

[0069] In a 5 mL three-neck flask under nitrogen protection, 16 mL of propargylamine was added, and then 6 g of mono-6-p-toluenesulfonyl-β-cyclodextrin was added, and heated to reflux at 90° C. for 24 hours. After cooling to room temperature under nitrogen protection, the reaction system was poured into 90 mL of acetonitrile to precipitate a solid. The solid was washed twice with acetonitrile to obtain the product mono-6-deoxy-N-propargylamino-β-cyclodextrin.

[0070]Add 50 mL of distilled water to a 10 mL three-necked flask, then add 5 g of mono-6-p-toluenesulfonyl-β-cyclodextrin, then add 1.26 g of sodium azide, and heat to 85° C. for 20 hours. The reaction system was poured into 25 mL of acetone to precipitate a solid. The solid was washed twice with acetone to obtain mono-6-deoxy-azido-β-cyclodextrin.

[0071] Add 5mL of anhydrous DMF to a 100mL three-necked flask, then add 1.74g of mono-6-deoxy-azido-β-cyclodextrin, then add 0.27g of sodium hydride (95%), and stir the r...

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Abstract

The invention discloses a preparation method of a novel triazole bridging compound cyclodextrin chiral stationary phase. The preparation method comprises the following two steps: firstly, introducing azido mono-substituted cyclodextrin on the surface of silica gel through an ether bond by utilizing a silane coupling agent; then, bonding alkynyl substituted cyclodextrin on the surface of azido cyclodextrin silica gel through cuprous catalyzed 1,3-dipolar cycloaddition reaction (click chemistry) so as to prepare the triazole bridging compound cyclodextrin silica gel chiral stationary phase with a good synergistic effect. The stationary phase prepared by the invention shows excellent separation ability to different drugs, such as dansyl amino acid, micromolecular aromatic acid and neutral racemic form, in liquid chromatogram, and therefore, the stationary phase prepared by the invention can be used as the chromatographic chiral stationary phase applied in the field of drug chiral separation.

Description

technical field [0001] The invention belongs to the field of chiral separation of drug racemates, and relates to a chromatographic chiral stationary phase. A series of novel cyclodextrin chiral molecules are prepared by constructing complex cyclodextrin chiral molecules on the surface of silica gel in a bottom-up manner. Dextrin chiral stationary phase can be used for chiral resolution and preparation of drugs in various chromatographic techniques. Background technique [0002] Chiral drugs have become a research hotspot in the field of medicine. The pharmacological activity, metabolic process, rate and toxicity of the two enantiomers of many drugs are significantly different in vivo. Single-enantiomer chiral drugs can not only eliminate the toxic and side effects of ineffective (bad) enantiomers, but also reduce the metabolic burden and improve drug specificity. Chiral separation is an effective means to obtain a single enantiomer, which has become a hot and difficult poi...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30
Inventor 王勇赵杰
Owner TIANJIN UNIV
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