Beta-cyclodextrin derivative, preparation thereof and use as chiral selector

A technology of cyclodextrin and derivatives, which is applied in the field of fully substituted p-halogenated phenyl β-cyclodextrin derivatives and its preparation, can solve the problems of inability to separate chiral compounds and low separation efficiency, and achieve strong chiral recognition ability, wide range of raw material sources, and mild reaction conditions

Inactive Publication Date: 2009-02-25
广州研创生物技术发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the common disadvantage of cyclodextrin chiral selectors in the prior art is that the separation efficiency is not high, and some chiral compounds cannot be separated

Method used

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  • Beta-cyclodextrin derivative, preparation thereof and use as chiral selector
  • Beta-cyclodextrin derivative, preparation thereof and use as chiral selector
  • Beta-cyclodextrin derivative, preparation thereof and use as chiral selector

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Preparation of SAZ-ClPh-β-CD

[0040] (1)6 A Preparation of -O-P-methylbenzenesulfonyl-β-cyclodextrin:

[0041] In a three-neck flask equipped with a magnetic stirrer and a thermometer, 30 ml of pyridine was used as a solvent, and 20 mmol of β-cyclodextrin and 16 mmol of p-toluenesulfonyl chloride were sequentially added. The reaction conditions were controlled at 25±2°C, and the reaction time was 20 hours; after the reaction was completed, pyridine was evaporated under reduced pressure, washed 3 times with 200ml acetone each time, and the white product TS-β-CD was obtained after vacuum drying, with a yield of about 8 gram;

[0042] (2)6 A -Azide-6 A - Preparation of deoxy-β-cyclodextrin:

[0043] Take TS-β-CD 6mmol obtained in step (1) and sodium azide 124mmol, add 400ml of ion-free water, and in a three-necked flask equipped with a magnetic stirrer, a thermometer and a reflux condenser, control the reaction temperature to be 60-65 °C, the reaction time...

Embodiment 2

[0046] Example 2 Preparation of SAZ-ClPh-β-CD

[0047] (1)6 A Preparation of -O-P-methylbenzenesulfonyl-β-cyclodextrin:

[0048] In a three-necked flask equipped with a magnetic stirrer and a thermometer, 30 ml of pyridine was used as a solvent, and 20 mmol of β-cyclodextrin and 18 mmol of p-toluenesulfonyl chloride were sequentially added. The reaction conditions were controlled at 25±2°C, and the reaction time was 24 hours. After the reaction, the pyridine was evaporated under reduced pressure, washed three times with 200ml acetone each time, and about 8.8 grams of white product TS-β-CD was obtained after vacuum drying.

[0049] (2)6 A -Azide-6 A - Preparation of deoxy-β-cyclodextrin:

[0050] Take 6 mmol of TS-β-CD obtained in step (1) and 132 mmol of sodium azide, add 400 ml of ion-free water, and in a three-necked flask equipped with a magnetic stirrer, a thermometer and a reflux condenser, control the reaction temperature to be 85 to 90 °C, the reaction time is 4h; ...

Embodiment 3

[0055] Example 3 Preparation of MAZ-ClPh-β-CD)

[0056] (1) Seven replaces 6 A - Preparation of I-β-cyclodextrin:

[0057] In a three-necked flask equipped with a magnetic stirrer and a thermometer, 60 ml of dichloroethane was used as a solvent, and 20 mmol of β-cyclodextrin, 160 mmol of iodine, 140 mmol of triphenylphosphine, and 140 mmol of imidazole were sequentially added. Control the reaction condition to be 25±2°C, and the reaction time is 3h under the protection of nitrogen; after the reaction is completed, filter and remove the filtrate, wash the solid with 80ml ether 3 times each time, and vacuum dry to obtain the yellow product heptasubstituted 6 A -I-β-CD11 grams or so.

[0058] (2) Seven replaces 6 A -Azide-6 A - Preparation of deoxy-β-cyclodextrin:

[0059] Take step (1) gained seven to replace 6 A -I-β-CD 6mmol and sodium azide 848mmol were added into 600ml deionized water, and in a three-necked flask equipped with a magnetic stirrer, a thermometer and a re...

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Abstract

The invention discloses a beta-cyclodextrin derivative, a preparation method and the application that the beta-cyclodextrin derivative is taken as chiral selective agent; the derivative is formed on the basis that hydrogen on beta-cyclodextrin hydroxide radical is respectively replaced by XC6H5NHCO- and -N3, and has the general molecular formula of ((XC6H5NHCO) n (C42H49O34) (N3) m); the structural formula is shown as formula (I). The beta-cyclodextrin derivative has wide material source, mild reaction conditions and low cost; when beta-cyclodextrin derivative is taken as chiral selective agent, the chiral compound separated by the derivative has board application scope and good effect; furthermore, when the chiral selective agent is linked with matrix, the fastness level, density and chiral selectivity can be adjusted and controlled by manpower.

Description

technical field [0001] The invention belongs to the technical field of β-cyclodextrin chiral selectors, in particular to a fully substituted p-halogenated phenyl β-cyclodextrin derivative that can be used in chemically bonded chiral stationary phases and a preparation method thereof. The use of selective agents. Background technique [0002] The identification of chiral isomers and the determination of component content are very important, especially for some chiral drug molecules, because different chiral molecules have completely different biological activities in living systems. Chirality is like the "bricks and stones of building life". For example, sugars tend to have D-configuration in the process of life, while almost all amino acids exist in L-configuration. Life is built according to this D and L configuration. up. Since the function of most drugs is manifested through the interaction with chiral biological substances. The isomers of each chiral drug may exhibit ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16B01J20/29
Inventor 章伟光张振宾
Owner 广州研创生物技术发展有限公司
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