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A kind of preparation method and application of ω-diamine derivatized β-cyclodextrin bonded SBA-15 chiral stationary phase

A technology of chiral stationary phase and cyclodextrin, which is applied in the chemical field, can solve the problems affecting chiral separation effect, batch-to-batch chromatographic separation performance of difficult chiral stationary phase, and cyclodextrin port congestion, etc., so as to improve chiral separation High energy, abundant chiral recognition sites, cheap price

Inactive Publication Date: 2017-02-22
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, cyclodextrin derivatization methods mainly include methylation, acetylation, benzoylation, phenylcarbamate, etc., and most of them are full derivatization or partial derivatization. Due to the uncertainty of degree of substitution or position , it is difficult to ensure and effectively control the batch-to-batch chromatographic separation performance of the prepared chiral stationary phase, and the full derivatization sometimes causes the congestion of the cyclodextrin port, which affects the chiral separation effect

Method used

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  • A kind of preparation method and application of ω-diamine derivatized β-cyclodextrin bonded SBA-15 chiral stationary phase
  • A kind of preparation method and application of ω-diamine derivatized β-cyclodextrin bonded SBA-15 chiral stationary phase
  • A kind of preparation method and application of ω-diamine derivatized β-cyclodextrin bonded SBA-15 chiral stationary phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Take SBA-15 (400 m 2 / g) Activated silica gel 2.5 g as the base.

[0034] (1) Under nitrogen atmosphere, according to the ratio of 6-p-toluenesulfonylated β-cyclodextrin (mmol):ethylenediamine (ml) of 1.0:15, 6-p-toluenesulfonylated β-cyclodextrin Add alcohol and ethylenediamine into a round bottom flask, stir for 0.5 h 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 4 hours in an oil bath at 80° C. under the protection of nitrogen. Then evaporate the solvent under reduced pressure, dissolve the solid in a small amount of hot water, add acetone-water solution (10:1, v / v) under stirring, collect the white precipitate, and repeat the above operation 3 times, and dry in a vacuum oven at 40°C Finally, 6-ethylenediamino-β-cyclodextrin is obtained, and the reaction yield of this step is 60%;

[0035] (2) Under nitrogen atmosphere, according to 6-ethylened...

Embodiment 2

[0042] Take SBA-15 (500 m 2 / g) Activated silica gel 2.5 g as the base.

[0043] (1) Under nitrogen atmosphere, according to the ratio of 6-p-toluenesulfonylated β-cyclodextrin (mmol):ethylenediamine (ml) of 1.0:20, 6-p-toluenesulfonylated β-cyclodextrin Add alcohol and ethylenediamine into a round bottom flask, stir for 1 h 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 6 h in an oil bath at 85 °C under the protection of nitrogen. Then evaporate the solvent under reduced pressure, dissolve the solid in a small amount of hot water, add acetone-water solution (10:1, v / v) under stirring, collect the white precipitate, and repeat the above operation 3 times, and dry in a vacuum oven at 40°C Finally, 6-ethylenediamino-β-cyclodextrin is obtained, and the reaction yield of this step is 65%;

[0044] (2) Under a nitrogen atmosphere, according to 6-ethylenediamin...

Embodiment 3

[0051] Take SBA-15 (420 m 2 / g) Activated silica gel 2.5 g as the base.

[0052] (1) Under nitrogen atmosphere, according to the ratio of 6-p-toluenesulfonylated β-cyclodextrin (mmol): butanediamine (ml) is 1.0:16, 6-p-toluenesulfonylated β-cyclodextrin Add alcohol and butylenediamine into a round bottom flask, stir for 0.8 h 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 5 hours in an oil bath at 85° C. under the protection of nitrogen. Then evaporate the solvent under reduced pressure, dissolve the solid in a small amount of hot water, add acetone-water solution (10:1, v / v) under stirring, collect the white precipitate, and repeat the above operation 3 times, and dry in a vacuum oven at 40°C Finally, 6-butanediamino-β-cyclodextrin was obtained, and the reaction yield of this step was 58%;

[0053] (2) Under nitrogen atmosphere, according to 6-butanediam...

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Abstract

The invention relates to a preparation method and an application of an omega-diamine derivatization beta-cyclodextrin bonded SBA-15 chiral stationary phase. The preparation method comprises steps as follows: 6-p-tosylation beta-cyclodextrin and omega-diamine are taken as raw materials, the omega-diamine is a solvent, and 6-(omega-diamine)-beta-cyclodextrin ligand is prepared through heating; the 6-(omega-diamine)-beta-cyclodextrin ligand and 3-isocyanato propyl siloxane react to prepare siloxane containing the 6-(omega-diamine)-beta-cyclodextrin ligand; anhydrous N,N-dimethyl formamide is taken as a solvent and heated under the protection of nitrogen, so that the siloxane containing the 6-(omega-diamine)-beta-cyclodextrin ligand reacts with a silanol hydroxyl group on the surface of SBA-15 silica gel, and a coarse product is obtained; and redundant ligand and impurities in holes are cleared, and a final product is obtained. The preparation method is simple, convenient, lower in cost, wide in application and suitable for rapidly preparing the chiral stationary phase.

Description

technical field [0001] The invention belongs to the field of chemistry and relates to a preparation method and application of a bonded SBA-15 silica gel chiral stationary phase. Background technique [0002] Chirality is one of the basic properties of nature, which refers to the property that a substance and its mirror image cannot overlap. Chirality is closely related to living substances. Various proteins, biological enzymes, nucleic acids, and active polysaccharides contained in the human body are chiral, and they often show a high degree of stereoselectivity when interacting with chiral drugs, making chiral drugs Enantiomers exhibit different pharmaceutical activities and toxic effects. Generally, only one enantiomer has pharmaceutical activity, while the activity of the other is weak or inactive, and even has toxic side effects. For example, β-blockers are the most common first-line chiral drugs for the clinical treatment of hypertension, cardiovascular and cerebrovas...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G81/00C08B37/16B01J20/29B01J20/30
Inventor 李来生程彪平黄志兵周仁丹聂桂珍张宏福
Owner NANCHANG UNIV
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