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Preparation method and application of a naphthaloyl bridged double β-cyclodextrin bonded chiral stationary phase

A technology of naphthaloyl bridge and chiral stationary phase, which is applied in chemical instruments and methods, and other chemical processes, can solve the problems of no mandatory chiral detection, etc., and achieve good enantiomeric selectivity, stable chromatographic performance, Good batch-to-batch reproducibility

Active Publication Date: 2022-05-20
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In 2006, my country's Food and Drug Administration also promulgated the "Technical Guidelines for Quality Control Research of Chiral Drugs", and there is no mandatory chiral testing
And the naphthaloyl bridged double β-cyclodextrin stationary phase prepared by the present invention can completely resolve the above-mentioned solute (in the accompanying drawing image 3 ), consult the relevant literature, and there is no relevant report on the preparation and use of this stationary phase at home and abroad.

Method used

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  • Preparation method and application of a naphthaloyl bridged double β-cyclodextrin bonded chiral stationary phase
  • Preparation method and application of a naphthaloyl bridged double β-cyclodextrin bonded chiral stationary phase
  • Preparation method and application of a naphthaloyl bridged double β-cyclodextrin bonded chiral stationary phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Take SBA-15 (400m 2 / g) 3.0 g of activated silica gel is used as the base.

[0029] (1) Mono-6-amino-β-cyclodextrin (mmol): 1,4-naphthalene dicarboxylic acid (mmol): DCC (mmol): NHS (mmol): DMF (mL) according to 1.0:0.5:0.5 : Mix and dissolve at a ratio of 0.5:10, and react at 20°C for 48 hours to obtain a solution containing naphthaloyl-bridged bis-β-cyclodextrin. According to mono-6-amino-β-cyclodextrin (mmol): The ratio of acetone (mL) is 1.0:80. After adding acetone to the above reaction solution, a white precipitate precipitates out, and then it is separated and purified by carboxymethyl dextran gel (C-25) column, and acetone is added to precipitate the product. After drying, it is obtained Naphthaloyl-bridged bis-β-cyclodextrin chiral ligands.

[0030] (2) Under nitrogen protection, according to the naphthaloyl-bridged bis-β-cyclodextrin in (1) (mmol): 3-isocyanatopropyltriethoxysilane (mL): anhydrous DMF Dissolve naphthaloyl-bridged bis-cyclodextrin in anhydro...

Embodiment 2

[0037] Take SBA-15 (400m 2 / g) 3.0 g of activated silica gel is used as the base.

[0038] (1) Mono-6-amino-β-cyclodextrin (mmol): 1,4-naphthalene dicarboxylic acid (mmol): DCC (mmol): NHS (mmol): DMF (mL) according to 1.0:1.5:1.5 : Mix and dissolve at a ratio of 1.5:15, and react at 20°C for 48 hours to obtain a solution containing naphthaloyl-bridged bis-β-cyclodextrin. According to mono-6-amino-β-cyclodextrin (mmol): The ratio of acetone (mL) is 1.0:80. After adding acetone to the above reaction solution, a white precipitate precipitates out, and then it is separated and purified by carboxymethyl dextran gel (C-25) column, and acetone is added to precipitate the product. After drying, it is obtained Naphthaloyl-bridged bis-β-cyclodextrin chiral ligands.

[0039] (2) Under nitrogen protection, according to (1) naphthaloyl bridged bis-β-cyclodextrin (mmol): 3-isocyanatopropyl triethoxysilane (mL): anhydrous DMF (mL) Dissolve naphthaloyl-bridged bis-β-cyclodextrin in anhydr...

Embodiment 3

[0046] Take SBA-15 (400m 2 / g) 3.0 g of activated silica gel is used as the base.

[0047] (1) Mono-6-amino-β-cyclodextrin (mmol): 1,4-naphthalene dicarboxylic acid (mmol): DCC (mmol): NHS (mmol): DMF (mL) according to 1.0:2.0:2.0 : Mix and dissolve at a ratio of 2.0:20, and react at 20°C for 48 hours to obtain a solution containing naphthaloyl-bridged bis-β-cyclodextrin. According to mono-6-amino-β-cyclodextrin (mmol): The ratio of acetone (mL) is 1.0:80. After adding acetone to the above reaction solution, a white precipitate precipitates out, and then it is separated and purified by carboxymethyl dextran gel (C-25) column, and acetone is added to precipitate the product. After drying, it is obtained Naphthaloyl-bridged bis-β-cyclodextrin chiral ligands.

[0048] (2) Under nitrogen protection, according to (1) naphthaloyl bridged bis-β-cyclodextrin (mmol): 3-isocyanatopropyl triethoxysilane (mL): anhydrous DMF (mL) Dissolve naphthaloyl-bridged bis-β-cyclodextrin in anhydr...

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Abstract

The invention discloses a preparation method of a naphthaloyl-bridged bis-β-cyclodextrin bonded chiral stationary phase, using naphthaloyl-bridged bis-β-cyclodextrin as a chiral stationary phase ligand, SBA-15 The naphthaloyl bridged bis-cyclodextrin bonded chiral separation material is a silica gel substrate, and the naphthaloyl bridged biscyclodextrin stationary phase of the present invention has obvious advantages in chiral separation. The traditional single β-cyclodextrin stationary phase cannot resolve substances such as flavanone (a), 4’-hydroxyflavanone (c), praziquantel (d), and imazalil (f). The naphthaloyl bridged double β-cyclodextrin stationary phase prepared by the invention can be completely resolved.

Description

technical field [0001] The invention relates to a preparation method and application of a bridged bicyclodextrin-bonded chiral stationary phase, which uses naphthalene diformyl bridged bis-cyclodextrin as a chiral stationary phase ligand and SBA-15 as a silica gel matrix A method for preparing a naphthaloyl bridged double β-cyclodextrin bonded chiral separation material. Background technique [0002] Due to the differences in the spatial structure of the atoms of chiral compounds, their enantiomers often exhibit highly stereoselective effects in biological activity, toxicity, and pharmacokinetics. The chirality problem caused by enantiomers has already attracted widespread attention from the international community [Martinez, Nutr. Food. Res, 2015]. For example, in the early 1960s, due to pregnant women taking racemic drugs, the "thalidomide incident" that shocked the world occurred, resulting in the birth of about 12,000 deformed babies. It was later proved that S-thalidom...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/29B01J20/30
CPCB01J20/29B01J2220/4812B01J2220/80B01J2220/52B01J2220/54
Inventor 李来生双亚洲李良张天赐钟慧
Owner NANCHANG UNIV
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