Optically pure mandelic acid derivative-cellulose chiral stationary phase, preparation method and application

A technology of cellulose and mandelic acid, which is applied in the field of chiral chromatographic separation, can solve the problems that have not been reported in the literature, and achieve the effects of low cost, good selectivity, and easy preparation

Active Publication Date: 2021-12-17
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the above-mentioned cellulose chiral stationary phase, in the derivatization process of cellulose, the selected derivatization reagents are all achiral reagents (such as achiral acid halides), and the relevant chiral reagents (such as chiral acid halides) are The method of derivatizing free hydroxyl groups at the 2,3,6-position of cellulose and then preparing a chiral stationary phase has not been reported in the literature.

Method used

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  • Optically pure mandelic acid derivative-cellulose chiral stationary phase, preparation method and application
  • Optically pure mandelic acid derivative-cellulose chiral stationary phase, preparation method and application
  • Optically pure mandelic acid derivative-cellulose chiral stationary phase, preparation method and application

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Effect test

Embodiment 1

[0090] Embodiment 1.2,3, the synthesis of 6-trimandelic acid acyl cellulose CSP-A1 ( Figure 4 )

[0091] Steps:

[0092] Under argon atmosphere, (S)-mandelic acid (compound 1, 15.20 g, optical purity >98%) was suspended in 15 mL of dry pyridine and 200 mL of dry dichloromethane (CH 2 Cl 2 ), stirred and cooled to -5°C. After 15 minutes, slowly drop in 7.5mL of freshly distilled acetyl chloride (AcCl) with a syringe, and the dropwise addition is completed within 10 minutes. The reaction solution naturally rose to room temperature, stirred for 8 h, evaporated the solvent under reduced pressure, added 200 mL of dichloromethane to the obtained residue, and washed with deionized water (50 mL), saturated aqueous ammonium chloride solution (50 mL), and deionized water (50 mL) successively. , saturated brine (50mL), washed with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 19.2 grams (99% yield) of a light yellow viscous product, which ...

Embodiment 2

[0094] Embodiment 2.2,3, the synthesis of 6-trimandelic acid acyl cellulose CSP-A2 ( Figure 5 )

[0095] Steps:

[0096] It is only necessary to replace the acetyl chloride in Example 1 with benzoyl chloride, and the rest of the operation steps are the same as in Example 1 to obtain 2,3,6-trimandelic acid acyl cellulose CSP- A2 (9.2g), placed in a vacuum oven for later use. Infrared analysis IR(cm -1 ): 1720 (C=O), 1650 (Ar), 1555 (Ar).

Embodiment 3

[0097] Embodiment 3.2,3, the synthesis of 6-trimandelic acid acyl cellulose CSP-A3 ( Image 6 )

[0098] Steps:

[0099] It is only necessary to replace the acetyl chloride in Example 1 with 4-methylbenzoyl chloride, and the rest of the operation steps are the same as in Example 1, and the 2,3,6-trimandelic acid acyl group used for coating chiral column packing can be obtained Cellulose CSP-A3 (9.7g), placed in a vacuum oven for later use. Infrared analysis IR(cm -1 ): 1726 (C=O), 1676 (Ar), 1535 (Ar).

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Abstract

The invention discloses an optically pure mandelic acid derivative-cellulose chiral stationary phase, a preparation method and an application. Use optically pure mandelic acid or optically pure mandelic acid derivative acid halide and microcrystalline cellulose to prepare chiral chromatography column precursor, and coat or bond on the surface of chromatography-grade silica gel to form chiral column packing, which is further prepared Stainless steel chiral column can be used for the separation and analysis of various chiral substances.

Description

technical field [0001] The invention belongs to the technical field of chiral chromatographic separation, and relates to the structure and preparation method of an optically pure mandelic acid derivative-cellulose chiral stationary phase and its application in the separation of chiral compounds. Background technique [0002] As one of the best methods for analyzing, separating and preparing chiral compounds, high-performance liquid chromatography (HPLC) has always been valued by analytical scientists. The identification and separation of chiral compounds by HPLC relies critically on chiral stationary phases (CSP). The chiral stationary phase is prepared by immobilizing chiral units on matrix materials such as silica gel and seaweed. Through the difference between the microenvironment of the chiral stationary phase and the effect of enantiomers, the separation of various optical isomers can be achieved. . [0003] It has long been recognized that polysaccharides (such as st...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/29G01N30/02
CPCG01N30/02B01J20/29G01N2030/027
Inventor 贾艳艳崔冬晓王平安文爱东孙晓莉李广庆
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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