Borono benzoylated beta-cyclodextrin bonded silica gel and uses thereof

A technology of boronic acid benzoyl and acid benzoyl, which is applied in the field of preparation of bonded SBA-15 silica gel chiral stationary phase, and can solve the problems of poor chiral separation performance of chiral stationary phase materials and the like

Inactive Publication Date: 2016-10-26
NANCHANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention aims at the technical defects of the prior art, and provides a boronic acid group benzoylated β-cyclodextrin bonded silica gel to solve the poor chiral separation performance of chiral stationary phase materials in the prior art question

Method used

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  • Borono benzoylated beta-cyclodextrin bonded silica gel and uses thereof
  • Borono benzoylated beta-cyclodextrin bonded silica gel and uses thereof
  • Borono benzoylated beta-cyclodextrin bonded silica gel and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] A kind of boronic acid group benzoylation β-cyclodextrin bonded silica gel, is prepared by following method:

[0072]1) Under a nitrogen atmosphere, use anhydrous dimethyl sulfoxide as a solvent, and use the mmol dosage of ethylenediamine β-cyclodextrin as the raw material: the mmol dosage of (o-, m-, p-)-carboxyphenylboronic acid: dimethyl The ratio of the amount of sulfoxide in ml is 1.0:0.6~1.0:40~50, add 2.0~4.0mmol N-hydroxysuccinimide, 2.0~3.0mmol1-ethyl-3-(3-dimethylaminopropyl ) carbodiimide hydrochloride, stirring for 1-2 hours to fully dissolve the raw materials to form a homogeneous solution; in an oil bath at 35-40 ° C, magnetically stirred for 18-20 hours; then filtered and mixed with dimethyl sulfoxide, water, After washing with methanol and acetone in sequence, and drying in vacuum at 50°C, the boronic acid-benzoylated β-cyclodextrin ligand is obtained;

[0073] 2) Under a nitrogen atmosphere, dissolve the borate-benzoylated β-cyclodextrin obtained in st...

Embodiment 2

[0087] Take SBA-15 (400m 2 / g) Activated silica gel 2.5g as the base.

[0088] 1) Under a nitrogen atmosphere, use anhydrous dimethyl sulfoxide as a solvent, and prepare the raw materials according to the mmol amount of ethylenediamine β-cyclodextrin: the mmol amount of o-carboxyphenylboronic acid: the ml amount of dimethyl sulfoxide Add the ratio of 1.0:0.6:40 to the round bottom flask, add 2.0mmol N-hydroxysuccinimide, 2.0mmol 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride Salt, stir for 1 hour to fully dissolve the raw materials to form a homogeneous solution; configure a condenser tube and a calcium chloride drying tube, and react with magnetic stirring for 18 hours in an oil bath at 35°C; then filter and mix with dimethyl sulfoxide, water, methanol, After washing with acetone in sequence and vacuum drying at 50°C, o-boronic acid benzoylated β-cyclodextrin was obtained, and the reaction yield of this step was 55%;

[0089] 2) Under a nitrogen atmosphere, dis...

Embodiment 3

[0096] Take SBA-15 (500m 2 / g) Activated silica gel 2.5g as the base.

[0097] 1) Under a nitrogen atmosphere, use anhydrous dimethyl sulfoxide as a solvent, and prepare the raw materials according to the mmol amount of ethylenediamine β-cyclodextrin: the mmol amount of o-carboxyphenylboronic acid: the ml amount of dimethyl sulfoxide Add the ratio of 1.0:1.0:50 to the round bottom flask, add 4.0mmol N-hydroxysuccinimide, 3.0mmol 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride Salt, stir for 2 hours to fully dissolve the raw materials to form a homogeneous solution; configure a condenser tube and a calcium chloride drying tube, and react with magnetic stirring for 20 hours in a 40°C oil bath. Then, after filtering, washing with dimethyl sulfoxide, water, methanol and acetone in sequence, and vacuum-drying at 50°C, the o-boronic acid benzoylated β-cyclodextrin ligand was obtained, and the reaction yield of this step was 67%;

[0098] 2) Under a nitrogen atmosphere,...

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Abstract

Borono benzoylated beta-cyclodextrin bonded silica gel and uses thereof are provided. According to a technical scheme, a borono benzoylated beta-cyclodextrin ligand is firstly prepared by adopting ethylenediamine-beta-cyclodextrin, dicarboxyphenylboronic acid, N-hydroxysuccinimide and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride as raw materials, and then a novel chiral stationary phase is prepared by adopting 3-isocyanato propylsiloxane as a coupling agent and adopting ordered mesopores SBA-15 silica gel as a bonding substrate. The bonded silica gel enriches chiral recognition sites through bonding a phenylboronic acid port substitute and a cyclodextrin cavity, and can generate chiral recognition functions with a neutral solute and an ionized solute through hydrogen bonds, dipoles, pi-pi, charge transfer, inclusion, and other synergistic effects, thus improving chiral separation capability and a chiral separation range. Test results prove that the bonded silica gel is large in specific area and high in bonding amount, and a chromatographic column is long in service lifetime because cyclodextrin is stable in performance and connected to the silica gel in a bonding manner.

Description

technical field [0001] The present invention relates to the technical field of organic synthesis, and further relates to the preparation method and application of bonded SBA-15 silica gel chiral stationary phase, in particular to bonded SBA-15 silica gel with derivatized β-cyclodextrin containing phenylboronic acid group as ligand Preparation method of chiral stationary phase and use of chiral separation. Background technique [0002] Chiral compounds refer to compounds that have the same molecular formula but differ in spatial orientation of the atoms that make up the compound, forming a pair of mirror-image isomers. More than 40% of synthetic drugs and 30% of pesticides have chiral centers, most of which are sold and used in the form of racemic mixtures. Although the left-handed and right-handed compounds have the same physical and chemical properties except the deflection direction of polarized light, the study found that the S-type enantiomer and the R-type enantiomer h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29B01J20/30C08B37/16B01D15/38
CPCB01D15/3833B01J20/29C08B37/0012
Inventor 李来生曾春周仁丹程彪平曹志刚李良张宏福廖玉芹
Owner NANCHANG UNIV
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