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

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

CN101235104AInactive Publication Date: 2008-08-06BEIJING INSTITUTE OF TECHNOLOGYGY
0 Cites 14 Cited by

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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
Comparison scheme
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%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
06 Aug 2008
Publication
CN101235104A
IPC
C08B37/16; C07B57/00; C07B53/00; B01J31/06
CPC
Y02P20/584
Inventors
周智明; 陈晓平