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Method for preparing 4-hydroxyl tetrahydropyran derivative with optical activity through enzymatic transesterification

A technology of hydroxytetrahydropyran derivatives and optical activity, which is applied in the field of preparation of magnetic inorganic-organic complex immobilized enzymes as catalysts, can solve the problems of easy clustering deactivation, mechanical loss, poor stability, etc., and achieve The effect of high reaction enantioselectivity, no mechanical loss, and high stability

Inactive Publication Date: 2013-07-10
NINGXIA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, free lipase is easily clustered and inactivated in organic solvents, has poor stability, is difficult to separate, and suffers severe mechanical loss during repeated use. These problems limit the practical application of enzyme-catalyzed methods.

Method used

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  • Method for preparing 4-hydroxyl tetrahydropyran derivative with optical activity through enzymatic transesterification
  • Method for preparing 4-hydroxyl tetrahydropyran derivative with optical activity through enzymatic transesterification
  • Method for preparing 4-hydroxyl tetrahydropyran derivative with optical activity through enzymatic transesterification

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]Example 1 Preparation of Optically Active 2-Phenyl-4-Hydroxytetrahydropyran and Its Acetate by Enzyme-Catalyzed Transesterification

[0031] Add 0.05mol of 2-benzene-4-hydroxytetrahydropyran and 0.05mol of vinyl acetate into a 250ml reactor, then add 100ml of heptane and mix well, then add 0.1g of magnetic Fe 3 o 4 SiO 2 -(CH 2 ) 3 -NH 2 Immobilized PSL enzyme, reacted under stirring at 30°C for 24 hours, separated the immobilized enzyme in a magnetic field, and obtained the enantiomer of the chiral enantiomer (2R, 4S)-2-benzene-4-hydroxytetrahydropyran body excess value ee s 99.0%, enantiomeric excess ee of (2S,4R)-2-phenyltetrahydropyran-4-ol acetate p was 88.6%.

Embodiment 2

[0032] Example 2 Preparation of Optically Active 2-Phenyl-4-Hydroxytetrahydropyran and Its Acetate by Enzyme-Catalyzed Transesterification

[0033] Add 0.05mol of 2-benzene-4-hydroxytetrahydropyran and 0.05mol of isopropenyl acetate into a 250ml reactor, then add 100ml of cyclohexane and mix well, then add 0.1g of magnetic MnFe 2 o 4 SiO 2 -(CH 2 ) 3 -NH 2 Immobilized PSL enzyme, reacted for 36 hours under stirring at 30°C, separated the immobilized enzyme in a magnetic field, and the content of the obtained chiral enantiomer was analyzed by chiral column high performance liquid chromatography, (2R, 4S)-2- Enantiomeric Excess Value ee of Benzene-4-Hydroxytetrahydropyran s 98.0%, enantiomeric excess value ee of (2S,4R)-2-phenyltetrahydropyran-4-ol acetate p was 87.6%.

Embodiment 3

[0034] Example 3 Preparation of Optically Active 2-Benzene-4-Hydroxytetrahydropyran and Its Acetate by Enzyme-Catalyzed Transesterification

[0035] Add 0.05mol of 2-benzene-4-hydroxytetrahydropyran and 0.05mol of vinyl acetate into a 250ml reactor, then add 100ml of toluene and mix well, then add 0.1g of magnetic MnFe 2 o 4 SiO 2 -(CH 2 ) 3 -NH 2 Immobilized CRL enzyme, reacted under stirring at 30°C for 24 hours, separated the immobilized enzyme in a magnetic field, and obtained the enantiomer of (2R, 4S)-2-benzene-4-hydroxytetrahydropyran body excess value ee s 99.0%, enantiomeric excess value ee of (2S,4R)-2-phenyltetrahydropyran-4-ol acetate p was 92.0%.

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Abstract

The invention discloses a method for a preparing 4-hydroxyl tetrahydropyran derivative with optical activity through enzymatic transesterification. The method comprises the following steps: adding a mixture of a racemic 4-hydroxyl tetrahydropyran derivative and an acyl donor with the molar ratio of 1:1 to 1:4 into an organic solvent; adding magnetic immobilized lipase; reacting under stirring at the temperature of 10 to 60 DEG C for 2 to 36 hours, wherein the relative using amount of the magnetic immobilized lipase and the racemic 4-hydroxyl tetrahydropyran derivative is controlled to be from 1mg:1ml to 100mg:1ml; separating out the immobilized enzyme from the magnetic field and stopping reaction; and performing column chromatographic separation to obtain the 4-hydroxyl tetrahydropyran derivative with optical activity and acetic acid ester of the derivative. The method is realized by utilizing high activity, high selectivity and high stability of the magnetic immobilized enzyme; the immobilized enzyme is separated quickly under the action of the magnetic field; mechanical loss is avoided; high-efficiency recycling is realized; the catalytic efficiency is high; the cost is low; and the process is simple and quick.

Description

technical field [0001] The invention relates to a method for splitting and preparing optically active 4-hydroxytetrahydropyran derivatives by enzyme-catalyzed transesterification reaction, in particular to a preparation method using a magnetic inorganic-organic compound immobilized enzyme as a catalyst. Background technique [0002] Tetrahydropyran is the key structural unit of polyether antibiotics. As a chiral building block, 4-hydroxytetrahydropyran compounds are important intermediates in the synthesis of many drugs. In drug synthesis, if a single enantiomer of 4-hydroxytetrahydropyran compounds is used as a raw material, the separation process of racemic drug molecules after chiral reagents will be omitted, and the utilization rate of raw materials and product quality will be improved. Therefore, it is of great significance to develop the preparation technology of single enantiomer of 4-hydroxytetrahydropyran derivatives. [0003] The methods for synthesizing tetrahydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P17/06
Inventor 薛屏康珍珍屈冠群李锐杨金会
Owner NINGXIA UNIVERSITY
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