Six kinds of alpha-schiff base derived beta-cyclodextrin and use

A technology of cyclodextrin and Schiff base, which is applied in the field of chiral stationary phase, can solve the problems of identifying single types of samples, single types of chiral columns, and chiral separation of new polymer chiral columns, so as to increase the chiral environment. Effect

Inactive Publication Date: 2008-08-06
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The molecular structure of this stationary phase is simple, the variety of samples identified during chiral separation is relatively narrow, and the application range is relatively narrow
In addition, although some polymer chiral stationary phase commercial columns, such as cyclodextrin commercial columns, have rich chiral environments, due to their complex molecular structures, commercial chiral columns have only a single variety, and the design of new polymer chiral columns and synthesis has become a bottleneck for chiral separations

Method used

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  • Six kinds of alpha-schiff base derived beta-cyclodextrin and use
  • Six kinds of alpha-schiff base derived beta-cyclodextrin and use
  • Six kinds of alpha-schiff base derived beta-cyclodextrin and use

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Such as figure 1 , add 3g of cyclodextrin aldehyde and 45ml of pyridine into a 100ml reaction bottle, start magnetic stirring, open the nitrogen protection valve, add 3.6g of L-phenylglycinol, control the temperature of the external heating equipment at 25-30°C, and stop the reaction after 4 days Heating and nitrogen protection, the reaction solution was dropped into acetone, cooled for 4 hours, filtered with suction, and the obtained solid was washed twice with acetone to obtain 6-L-phenylglycinolimine-β-cyclodextrin as a solid. The conversion rate of cyclodextrin aldehyde was 100%, and the yield of 6-L-phenylglycinol imine-β-cyclodextrin was 94%. The reaction conditions not mentioned in following each embodiment are identical with embodiment 1.

Embodiment 2

[0031] The conditions are the same as in Example 1, only the addition of L-phenylglycinol is changed to the addition of D-phenylglycinol. The reaction result is: the conversion rate of cyclodextrin aldehyde is 100%, and the conversion rate of 6-D-phenylglycinol imine-β - Cyclodextrin yield 96%.

Embodiment 3

[0033] The conditions are the same as in Example 1, except that the addition of L-phenylglycinol is changed to the addition of L-tyrosine. The reaction result is: the conversion rate of cyclodextrin aldehyde is 100%, and 6-L-tyrosine-β-cyclodextrin The imine yield was 93%.

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Abstract

The invention uses beta-cyclodextrin to synthesize six kinds of new beta-cyclodextrins derived from alpha-Schiff base and six chiral stationary phases thereof, wherein the invention reacts cyclodextrin aldehyde and six amine compounds to prepare beta-cyclodextrin derived from alpha-Schiff base, the compounds reacted with cyclodextrin aldehyde are L-phenylglycinol, D-phenylglycinol, L-tyrosine, D-tyrosine, L-tryptophan and D-tryptophan. The synthesis route is simple, with high yield, simple operation and easy purification. The invention can be used in chiral separation for the qualitative and quantitative research on optical isomer of amino acid, ferrocene amine compound, drug, sulfur-containing compound, alcohol compound, amino-compound and various chiral compounds. The invention can be used in asymmetry catalysis for recovering and circulating catalyst.

Description

Technical field [0001] The invention relates to the synthesis of novel alpha-Schiff base derivatized beta-cyclodextrin by using beta-cyclodextrin and the chiral stationary phase prepared therefrom, belonging to the field of chemical synthesis. Background technique [0002] In recent years, the rise of the chiral drug industry has led to the development of chiral separation. Due to its simple operation, fast separation speed and accurate analysis, chiral chromatography has been widely recognized by people and has become a hot spot in chiral separation research. In chiral chromatography, the chiral stationary phase is the key to separation, and it is often called the heart of chromatographic separation. [0003] β-cyclodextrins (β-CDs) are cyclic oligosaccharide cavity compounds composed of seven D-(+)-glucopyranose units linked by α-1,4 glycosidic bonds. Hydrophobic hydrogen atoms and sugar oxygen atoms, the outer hydrophilic hydroxyl. Because of its unique structure, cycl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16C07B57/00C07B53/00B01J31/06
CPCY02P20/584
Inventor 周智明陈晓平
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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