Method for preparing side-chain amylose with different carbamates and chiral stationary phase

A carbamate and amylose technology, applied in chemical instruments and methods, and other chemical processes, can solve problems such as poor chiral recognition ability, and achieve the effects of easy control, high yield, and wide sources

Inactive Publication Date: 2013-06-26
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, polysaccharide derivatives with aromatic ring substituents mainly have good chiral recognition and resolution performance for aromatic chiral compounds, while the chiral recognition ability for non-aromatic compounds without phenyl poor

Method used

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  • Method for preparing side-chain amylose with different carbamates and chiral stationary phase
  • Method for preparing side-chain amylose with different carbamates and chiral stationary phase
  • Method for preparing side-chain amylose with different carbamates and chiral stationary phase

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment approach 1

[0021] 1. Take 0.2g amylose and dry it in vacuum at 80°C for 4h, then stir and reflux in anhydrous N,N-dimethylacetamide for 12h; add 0.4g lithium chloride after cooling to room temperature; continue stirring for 2h , reheat to 70°C, add anhydrous pyridine, add excess triphenylchloromethane after reflux for 4h, stop the reaction after continuous stirring and reflux for 24h; cool to room temperature, add methanol to settle, filter and wash, and vacuum dry at 60°C to Constant weight, yield 88%.

[0022] 2. Continue vacuum drying the above intermediate product at 80°C for 4h, then reflux in anhydrous pyridine for 3h, then add excess 3,5-dimethylphenylisocyanate, continue to reflux at 80°C for 16h, then stop the reaction , washed well with methanol and dried in vacuo.

[0023] 3. The intermediate product obtained in the previous step was dissolved in a tetrahydrofuran solution containing a small amount of hydrochloric acid (1.8% by volume of tetrahydrofuran) for hydrolysis, and s...

specific Embodiment approach 2

[0027] 1. Take 0.2g amylose and dry it in vacuum at 80°C for 4h, then stir and reflux in anhydrous N,N-dimethylacetamide for 10h; add 0.4g lithium chloride after cooling to room temperature; continue stirring for 4h , reheat to 70°C, add anhydrous pyridine, add excess triphenylchloromethane after reflux for 3h, stop the reaction after continuous stirring and reflux for 24h; cool to room temperature, add methanol to settle, filter and wash, and vacuum dry at 60°C to Constant weight, yield 85%.

[0028] 2. Continue vacuum drying the above intermediate product at 80°C for 3h, then add excess 3,5-dichlorophenylisocyanate after reflux in anhydrous pyridine for 3h, stop the reaction after continuing to reflux at 80°C for 12h, Wash well with methanol and dry under vacuum.

[0029] 3. The intermediate product obtained in the previous step was dissolved in a tetrahydrofuran solution containing a small amount of hydrochloric acid (1.8% by volume of tetrahydrofuran) for hydrolysis, and ...

specific Embodiment approach 3

[0033] 1. Take 0.2g amylose and dry it in vacuum at 80°C for 4h, then stir and reflux in anhydrous N,N-dimethylacetamide for 10h; add 0.4g lithium chloride after cooling to room temperature; continue stirring for 4h , reheat to 70°C, add anhydrous pyridine, add excess triphenylchloromethane after reflux for 4h, stop the reaction after continuous stirring and reflux for 23h; cool to room temperature, add methanol to settle, filter and wash, and vacuum dry at 60°C to Constant weight, yield 90%.

[0034] 2. Continue to vacuum-dry the above-mentioned intermediate product at 80°C for 3 hours, then reflux in anhydrous pyridine for 4 hours, add excess 4-chlorophenyl isocyanate, continue to reflux at 80°C for 12 hours, and then stop the reaction. Wash and vacuum dry.

[0035] 3. The intermediate product obtained in the previous step was dissolved in a tetrahydrofuran solution containing a small amount of hydrochloric acid (1.9% by volume of tetrahydrofuran) for hydrolysis, and stirre...

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Abstract

The invention provides a method for preparing side-chain amylose with different carbamates and a chiral stationary phase. The method comprises the following steps of: carrying out vacuum drying on amylose, carrying out stirring reflux in anhydrous N,N-dimethyl acetamide, cooling to room temperature, then, adding lithium chloride, reheating, adding anhydrous pyridine, refluxing, then, adding superfluous triphenylchloromethane, and carrying out continuous stirring reflux; after vacuum drying, carrying out refluxing in the anhydrous pyridine, then, adding superfluous phenyl isocyanate, stopping reaction, completely washing by using methanol, and carrying out vacuum drying; dissolving into tetrahydrofuran solution containing hydrochloric acid so as to carry out hydrolysis; and fully dissolving into the anhydrous pyridine, adding superfluous cyclohexyl isocyanate, stopping reaction, adding methanol, and carrying out vacuum drying, thereby obtaining the side-chain amylose with the carbamates. According to the method, the adopted amylose is wide in source, is cheap and is easily available, and a synthesis process is simple, mature, easy to control and high in yield. The method can be applied to large-scale batch production.

Description

technical field [0001] The invention relates to a method for preparing amylose. The invention also relates to a preparation method of the amylose chiral stationary phase. Background technique [0002] At present, there are more than ten kinds of commercial polysaccharide chiral stationary phases (including cellulose and amylose), but all commercial chiral stationary phases are based on single-substituted polysaccharides Derivatives, that is, these derivatives have a single substituent at all three positions of the sugar unit. In order to develop new chiral stationary phases with high-efficiency broad-spectrum chiral recognition capabilities and expand the application range of chiral stationary phases, some attempts have been made to selectively substitute polysaccharide polymers. In 1993, the Okamoto research group first applied the regioselective substitution method to synthesize cellulose and starch derivatives with two phenyl carbamate groups at the 2-, 3- and 6-positio...

Claims

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Application Information

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IPC IPC(8): C08B33/00B01J20/29B01J20/30
Inventor 沈军刘双燕赵勇强
Owner HARBIN ENG UNIV
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