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Cyclodextrin derivative containing oxazoline segments as well as preparation and application of hydrogenated silica gel stationary phase bonded with cyclodextrin derivative

A technology containing oxazoline groups and cyclodextrins, applied in other chemical processes, organic chemistry, organic chemistry methods, etc., can solve problems such as shedding and interference in the separation process of reversed-phase chromatography, and achieves low polarity and is not easy to drag. Tail, high separation effect

Inactive Publication Date: 2015-04-29
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some residual free silanols are easy to absorb water and form a hydration film, which still causes some interference to the separation process of reversed-phase chromatography, and some chiral small molecules bonded to silanols are easy to absorb water under strong acid (pH<3) conditions. fall off

Method used

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  • Cyclodextrin derivative containing oxazoline segments as well as preparation and application of hydrogenated silica gel stationary phase bonded with cyclodextrin derivative
  • Cyclodextrin derivative containing oxazoline segments as well as preparation and application of hydrogenated silica gel stationary phase bonded with cyclodextrin derivative
  • Cyclodextrin derivative containing oxazoline segments as well as preparation and application of hydrogenated silica gel stationary phase bonded with cyclodextrin derivative

Examples

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Effect test

Embodiment example 1

[0024] The suspensions of R-POTPHDOCD-CSP and hydrogenated-R-POTPHDOCD-CSP were pumped into two chromatographic columns of 250mm×4.6mm (i.d.) specifications by homogenization method respectively, and were mixed in polar organic mode (acetonitrile / methanol / acetic acid / triethylamine) to measure the chromatographic properties of the two columns; the mobile phase was filtered through a 0.45 μm organic microporous membrane before use, and vacuum degassed for 30 minutes; the sample was dissolved in chromatographically pure methanol and filtered through a 0.45 μm needle filter ; The mobile phase flow rate is 0.6mL / min; The detection slope length is 254nm. See attached for separation data image 3 .

Embodiment example 2

[0026] The suspensions of R-POTPHDOCD-CSP and hydrogenated-R-POTPHDOCD-CSP were pumped into two chromatographic columns of 250mm×4.6mm (i.d.) specifications by homogenization method respectively, and were mixed in polar organic mode (acetonitrile / methanol / acetic acid / triethylamine) to measure the chromatographic properties of the two columns; the mobile phase was filtered through a 0.45 μm organic microporous membrane before use, and vacuum degassed for 30 minutes; the sample was dissolved in chromatographically pure methanol and filtered through a 0.45 μm needle filter ; The mobile phase flow rate is 0.6mL / min; The detection slope length is 254nm. See attached for separation data Figure 4 .

Embodiment example 3

[0028] The suspensions of R-POTPHDOCD-CSP and hydrogenated-R-POTPHDOCD-CSP were pumped into two chromatographic columns of 250mm×4.6mm (i.d.) specifications by homogenization method respectively, and were mixed in polar organic mode (acetonitrile / methanol / acetic acid / triethylamine) to measure the chromatographic properties of the two columns; the mobile phase was filtered through a 0.45 μm organic microporous membrane before use, and vacuum degassed for 30 minutes; the sample was dissolved in chromatographically pure methanol and filtered through a 0.45 μm needle filter ; The mobile phase flow rate is 0.6mL / min; The detection slope length is 254nm. See attached for separation data Figure 5 .

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Abstract

The invention provides a method for synthesizing a novel beta-cyclodextrin derivative modified by radicals containing oxazoline by using beta-cyclodextrin, and also provides a method for modifying the surface of common silica gel into hydrogenated silica gel and bonding the cyclodextrin derivative to the hydrogenated silica gel by using appropriate small molecules. An oxazoline derivative ligand used in the method provided by the invention has a very good rigid structure and a chiral recognition site, and is beneficial for improving the separation selectivity of a chiral selector to an enantiomer, and expanding the separation range of chiral compounds. According to the methods provided by the invention, 6-deoxy-6-R,S-(4-phenyl)-4,5-dihydrogen oxazoline-beta-cyclodextrin and 6-deoxy-6-R,S-(4-pyridine p-toluene sulfonate methyl)-4,5-dihydrogen oxazoline-beta-cyclodextrin are synthesized respectively by virtue of simple and easy operation steps, and are bonded to the hydrogenated silica gel to prepare a hydrogenated silica gel stationary phase. The whole synthetic route is simple in operation and mild in reaction condition, and the product is easy to purify and high in yield. The methods provided by the invention are applied to chiral separation, and are used for performing qualitative researches on certain chiral aromatic alcohols, ferrocene derivatives, amino acid and mandelic acid derivatives and chiral drugs in a polar organic mode and a reversed phase mode.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing a novel β-cyclodextrin derivative containing an oxazoline group by using β-cyclodextrin, and a stationary phase bonding method for bonding it to a hydrogenated silica gel substrate, belonging to the field of chemical synthesis . (2) Background technology [0002] The different roles of chiral enantiomers in physiological processes are increasingly recognized. Two different chiral molecules that are mirror images of each other often show different action characteristics in the fields of medicine, life, and catalysis. Therefore, it is more and more important to obtain optically pure single chiral isomers. [0003] At present, the resolution methods of chiral enantiomers can be mainly divided into three categories: chemical resolution, enzymatic or microbial resolution and chromatographic resolution. Among them, the chromatographic resolution method mainly utilizes the selective distribution of dif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16B01J20/29B01J20/30B01D15/38C07B57/00
Inventor 周智明王宇婷
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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