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Beta-cyclodextrin derivative capillary gas chromatography chiral fixed phase and preparing method thereof

A chiral stationary phase, gas chromatography technology, used in chemical instruments and methods, other chemical processes, etc., to achieve the effect of good stability

Inactive Publication Date: 2007-08-15
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention describes the introduction of allyl groups at the 2- and 3-positions of the β-cyclodextrin molecule, and the introduction of acyl groups at the 6-position to obtain novel β-cyclodextrin derivatives for use in capillary gas chromatography Chiral stationary phase, used for enantiomer separation, there is no report at home and abroad

Method used

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  • Beta-cyclodextrin derivative capillary gas chromatography chiral fixed phase and preparing method thereof
  • Beta-cyclodextrin derivative capillary gas chromatography chiral fixed phase and preparing method thereof
  • Beta-cyclodextrin derivative capillary gas chromatography chiral fixed phase and preparing method thereof

Examples

Experimental program
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Effect test

example 1

[0056] Example 1: Preparation of 6-O-tert-butyldimethylsilyl-β-cyclodextrin (6-O-TBS-β-cyclodextrin)

[0057]Dissolve 3.36g (2.96mmol) of β-cyclodextrin in 45 mL of dry pyridine, add dropwise 3.44g (22.78mmol) of tert-butyldimethylsilyl chloride in 30mL of dry pyridine solution at 0°C, and stir at 0°C for reaction 3 h, after stirring and reacting at room temperature overnight, pour into an equal amount of ice water, stir, and a white precipitate appears after standing, collect the white precipitate, wash twice with 200 mL of water, filter and dry to obtain the product.

[0058] 1 H NMR (300MHz, CDCl 3 ): 0.66ppm (6H, Si-C H 3 ), 0.87(9H, C(C H 3 ) 3 ), 3.3~4.0 (H on CD ring, 6H), 4.89~4.95 (1H, CD anomeric H), 5.2~5.31 (1H, O H ), 6.6~6.8 (1H, OH)

example 2

[0059] Example 2: Preparation of 2,3-di-O-allyl-6-O-tert-butyldimethylsilane-β-cyclodextrin

[0060] Add 2g of 50% sodium hydride into a three-necked flask, add 90mL of dry dimethylformamide (DMF), cool to 0°C, add dropwise 3g of 6-O-tert-butyldimethylsilyl-β-cyclodextrin (6- (O-TBS-β-cyclodextrin) in 60mL of DMF solution, after the dropwise addition, react at room temperature for 2 hours, cool to 0°C in an ice bath, add 8mL bromide propene dropwise, react under ice bath for 1 hour, and react at room temperature for 24 hours. After the reaction was completed, excess sodium hydride was removed with methanol, DMF was distilled off under reduced pressure, extracted with 50 mL of chloroform × 3, the chloroform layers were combined, washed twice with 50 mL of saturated sodium chloride water and three times with 50 mL of water, dried and reduced Concentrate under pressure to obtain the product.

[0061] IR (cm -1 ): 3080 (C=CH 2 ), 2940, 2900, 2860 (CH 2 , CH 3 ), 1643 (C=C), 1...

example 3

[0062] Example 3: Preparation of 2,3-di-O-allyl-β-cyclodextrin

[0063] 5mL tetrabutylammonium fluoride (1mol L -1 THF solution) was added to 3.1g of 2,3-di-O-allyl-6-O-tert-butyldimethylsilane-β-cyclodextrin in tetrahydrofuran (THF) 10mL solution, reflux reaction for 70min, and reduced pressure After concentration, 20 mL of chloroform was added to dissolve the product, and the chloroform layer was washed three times with 20 mL of saturated sodium chloride water and twice with 20 mL of water, dried over anhydrous sodium sulfate, and concentrated to obtain the product.

[0064] IR (cm -1 ): 3445(O-H), 3079(C=CH 2 ), 2940, 2924, 2850 (CH 3 , CH 2 ), 1644 (C=C), 1458, 1415, 1350 (CH 3 , CH 2 ), 1160, 1090, 1040 (C-O-C), 923 (CH=CH 2 ) 1 H NMR (300MHz, CDCl 3 ): 0.88 (C H 3 CH 2 ), 1.25 (CH 3 C H 2 ), 3.3-4.4 (CD ( H ), OC H 2 ), 5.0-5.28 (CD ( H ), CH=C H 2 ), 5.9 (C H =CH 2 )

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Abstract

The invention relates to a novel beta-cyclodextrin derivant capillary gas spectrum chiral fixed phase and relative preparation. The invention is characterized in that the invention leads allyl group with two keys into 2 and 3 positions of beta-cyclodextrin molecule, and leads valeryl group, enanthoyl group or caprylyl group into 6 position of beta-cyclodextrin molecule, to obtain novel beta-cyclodextrin detrivant. The inventive detrivant can be used as chiral fixed phase of capillary gas spectrum, with some chiral recognize ability to separate antimer of chiral compound.

Description

Technical field: [0001] The field that the present invention relates to is chiral chromatographic separation of enantiomers, and the novel β-cyclodextrin derivative capillary gas chromatographic chiral stationary phase described in the present invention is used for the separation of chiral chromatographic enantiomers. Background technique: [0002] Chirality is one of the essential attributes of nature that human beings depend on for survival. Biological macromolecules such as proteins, polysaccharides, and nucleic acids all have chirality. Optically active chiral substances widely exist in animals and plants. Studies have found that different enantiomers of medicines and pesticides with chiral centers have different biological activities, and some enantiomers even have toxic side effects. Therefore, obtaining optically pure medicines, pesticides, spices, flavors, food additives, new materials, etc. has become a research hotspot in the corresponding field, while identifying...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29
Inventor 史雪岩高希武梁沛
Owner CHINA AGRI UNIV
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