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Regioselective synthesis and application methods for amylose derivatives with different carbamate side groups

A carbamate, regioselective technology, applied in chemical instruments and methods, other chemical processes, etc.

Inactive Publication Date: 2015-11-04
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Until now, no synthetic method has been reported for selective substitution between the 2-, 6-, and 3-positions of the amylose sugar unit

Method used

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  • Regioselective synthesis and application methods for amylose derivatives with different carbamate side groups
  • Regioselective synthesis and application methods for amylose derivatives with different carbamate side groups
  • Regioselective synthesis and application methods for amylose derivatives with different carbamate side groups

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment approach 1

[0028] 1. Take 1g of amylose and vacuum-dry at 105°C for 4h, raise the temperature to 120°C, then stir and reflux in anhydrous N,N-dimethylacetamide for 4h; add 1.5g of lithium chloride after cooling to 100°C; Continue to stir for 2 hours, add 2.02 g of imidazole after cooling to room temperature; add excess dimethyl tert-hexyl silicon chloride after reflux for 20 minutes, reheat to 100 ° C, continue stirring and reflux for 24 hours to stop the reaction; cool to room temperature, add buffer ( Add 3.54 g of potassium dihydrogen phosphate and 7.14 g of dipotassium hydrogen phosphate to 1000 ml of distilled water), settle and filter, wash with ethanol and water (volume ratio 9:1), and vacuum-dry at 60° C. to constant weight. The yield is 80%.

[0029] 2. Vacuum-dry the above intermediate product at 80°C for 3h, then reflux in anhydrous pyridine for 6h, add excess 3,5-dichlorophenyl isocyanate after heating up to 100°C, continue to reflux at 100°C for 12h, then stop The reaction w...

specific Embodiment approach 2

[0034] 1. Take 1g of amylose and vacuum-dry at 105°C for 4h, raise the temperature to 120°C, then stir and reflux in anhydrous N,N-dimethylacetamide for 4h; add 1.5g of lithium chloride after cooling to 100°C; Continue to stir for 2 hours, add 2.02 g of imidazole after cooling to room temperature; add excess dimethyl tert-hexyl silicon chloride after reflux for 20 minutes, reheat to 100 ° C, continue stirring and reflux for 24 hours to stop the reaction; cool to room temperature, add buffer ( Add 3.54 g of potassium dihydrogen phosphate and 7.14 g of dipotassium hydrogen phosphate to 1000 ml of distilled water), settle and filter, wash with ethanol and water (volume ratio 9:1), and vacuum-dry at 60° C. to constant weight. The yield is 80%.

[0035] 2. Vacuum-dry the above intermediate product at 80°C for 4h, then reflux in anhydrous pyridine for 6h, heat up to 100°C, add excess 4-chlorophenyl isocyanate, continue to reflux at 100°C for 14h, then stop the reaction, use Wash tho...

specific Embodiment approach 3

[0040] 1. Take 1g of amylose and vacuum-dry at 105°C for 4h, raise the temperature to 120°C, then stir and reflux in anhydrous N,N-dimethylacetamide for 4h; add 1.5g of lithium chloride after cooling to 100°C; Continue to stir for 2 hours, add 2.02 g of imidazole after cooling to room temperature; add excess dimethyl tert-hexyl silicon chloride after reflux for 20 minutes, reheat to 100 ° C, continue stirring and reflux for 24 hours to stop the reaction; cool to room temperature, add buffer ( Add 3.54 g of potassium dihydrogen phosphate and 7.14 g of dipotassium hydrogen phosphate to 1000 ml of distilled water), settle and filter, wash with ethanol and water (volume ratio 9:1), and vacuum-dry at 60° C. to constant weight. The yield is 80%.

[0041] 2. Vacuum-dry the above intermediate product at 80°C for 4h, then reflux in anhydrous pyridine for 6h, add excess phenyl isocyanate after heating up to 100°C, stop the reaction after continuing to reflux at 100°C for 14h, and wash th...

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Abstract

The invention provides regioselective synthesis and application methods for amylose derivatives with different carbamate side groups. The synthesis method comprises taking amylose as an initial raw material, firstly introducing a tert-butyldimethylsilyl ester at 2- and 6- positions of a sugar unit of amylase as a protective group, then introducing a phenylcarbamic acid ester group at 3- position of the sugar unit, then in an alkali solution, removing the protective group and reducing hydroxyl at 2- and 6- positions, and finally introducing another kind phenylcarbamic acid ester group at 2- and 6- positions at the same time so as to finally realize regioselective synthesis of the amylose derivatives. On the basis, the synthesized novel amylose derivative is fully dissolved, the surface of silica gel is uniformly coated with the polymer through a coating process, and a column is packed by employing a homogenating process, so that a novel amylose chiral stationary phase is prepared. high performance liquid chromatography is applicable to detailed evaluation on the chiral recognition performance of the prepared chiral stationary phase.

Description

technical field [0001] The invention relates to a synthesis method of amylose derivatives and a preparation method of a chiral stationary phase. Background technique [0002] With the development of bioengineering and life sciences, people's demand for chiral stationary phase materials with new high-efficiency chiral recognition capabilities is increasing, and the requirements for chiral recognition efficiency and scope of application of chiral stationary phases are also getting higher and higher. . Until now, polysaccharides (especially starch and cellulose) derivatives are one of the most effective and widely used chiral stationary phase materials. This is because polysaccharides are the most abundant and important optically active polymers on the earth, and the hydroxyl groups at three positions on the glucose unit are easily substituted. Sex recognition ability is relatively good. Traditional amylose derivatives usually introduce substituents with the same structure a...

Claims

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Application Information

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IPC IPC(8): C08B33/00B01J20/29
Inventor 沈军杨忠正李庚赵勇强
Owner HARBIN ENG UNIV
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