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Cyclodextrin chiral chromatogram fixed phase and preparation method thereof

A chiral chromatography and cyclodextrin technology is applied in the field of cyclodextrin chiral chromatography stationary phase and its preparation, and achieves the effects of large surface bonding amount, few steps and avoiding side reactions

Inactive Publication Date: 2008-11-19
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the oligoethylene glycol chain has not been reported as the spacer arm of the cyclodextrin chiral stationary phase.

Method used

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  • Cyclodextrin chiral chromatogram fixed phase and preparation method thereof
  • Cyclodextrin chiral chromatogram fixed phase and preparation method thereof
  • Cyclodextrin chiral chromatogram fixed phase and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Step (1) In a 1000ml three-necked flask, add 400ml of anhydrous N, N dimethylformamide, 45mmol (10ml) 3-chloropropyltriethoxysilane, 60mmol (4.0g) sodium azide, and then add 3.0 Mmol sodium iodide (0.5g) was used as a catalyst, reacted at 80°C for 24h, and then added 20g of spherical silica gel particles were reacted at 80°C for another 24h, and then washed twice with dichloromethane, ethanol, water, and acetone, 200ml each time, and dried in vacuum for 12 hours to obtain (3-propyl)azidosilica gel .

[0044] Step (2) 250ml three-necked flask was added under nitrogen protection with 100ml tetrahydrofuran, 20mmol (4.00g) tetraethylene glycol, 43mmol (1.73g) 80% sodium hydride was added at 0°C, and 45mmol (3.5ml) bromine was added propyne. React at 0-5°C for 1 hour, then react at room temperature, use n-hexane / ethyl acetate (V:V=1:1) as a developing solvent, separate by thin-layer chromatography, and use potassium permanganate solution color development method Check wh...

Embodiment 2

[0049] During the preparation of (3-propyl)azido silica gel in Step (1) of Example 1, the reaction temperature was changed from 80°C to 60°C, or to 130°C, and the other steps were performed as in Example 1, or The cyclodextrin chiral chromatography stationary phase in Example 1 was obtained.

Embodiment 3

[0051] In embodiment 1 step (1) (3-propyl) azido base silica gel preparation process, adopt 400ml toluene to replace the solvent N in embodiment 1, N-dimethylformamide, other steps are operated according to embodiment 1 , the cyclodextrin chiral chromatography stationary phase in Example 1 is also available.

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Abstract

The invention discloses a cyclodextrin chiral stationary phase, the structure of which is shown in the general formula (I), wherein X is -OCH3 or -OCH2CH3, n is equal to 1-7, and R is -H, -CH3, -COCH3, -COC6H5 and -CONHC6H5. The preparation method of the stationary phase comprises the following steps: a silane coupling agent, sodium azide and a catalyst are added into an organic solvent, then spheroidal silicon is added for preparing azide silica gel derivant; oligomeric ethylene glycol, sodium hydride and propargyl bromide are added into tetrahydrofuran for preparing bialkynyl oligomeric ethylene glycol; monosubstituted nascent and derivative cyclodextrin containing azid groups is prepared; finally, the click chemistry reaction method is used for bonding the cyclodextrin. The cyclodextrin chiral stationary phase has the advantages that the selectivity of the bonding reaction is high, and the surface bonded amount is large; the chiral separation ability is strong, thereby being especially suitable for the chiral separation of a high efficiency liquid chromatography in the reversed-phase mode; the preparation method is simple and has less steps, the bonding reaction is the click chemistry reaction, the reaction condition is mild, and the reaction is carried out in the water solution.

Description

technical field [0001] The invention relates to a cyclodextrin chiral chromatographic stationary phase and a preparation method thereof. Specifically, oligoethylene glycol is used as a spacer arm and click chemistry is used as a bonding method to prepare a cyclodextrin chiral phase. Chromatographic stationary phase. Background technique [0002] Cyclodextrin (hereinafter referred to as CD) is a kind of cyclic oligosaccharides composed of different numbers of glucopyranose units in chair conformation linked by α-1,4-glycosidic bonds, the common ones are 6,7 , 8-mer, namely α, β, γ-CD. Each glucose unit has 5 chiral centers, and the CD composed of n glucose units has 5n chiral centers, which provides a good asymmetric environment for chiral recognition. In addition, the 2, 3, and 6 hydroxyl groups on the CD molecule can be selectively modified to prepare chiral selectors with different properties due to their different reactivity. For the preparation of cyclodextrin chiral ...

Claims

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Application Information

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IPC IPC(8): B01J20/29
Inventor 梁鑫淼张永平郭志谋叶金星徐青雷爱文
Owner EAST CHINA UNIV OF SCI & TECH
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