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Method for preparing (S)-3-hydroxytetrahydrofuran based on erythritol microorganisms

A hydroxytetrahydrofuran and microorganism technology, which is applied to microorganism-based methods, biochemical equipment and methods, microorganisms, etc., can solve the problem of not many choices, and achieve the effects of simplified steps, low cost, and mild reaction.

Inactive Publication Date: 2016-06-01
ITIC MEDCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current technology for preparing (R)-3-hydroxytetrahydrofuran based on microbial agents is still immature, and there are not many options. The preparation market of tetrahydrofuran promotes the production of (R)-3-hydroxytetrahydrofuran, and then assists the development of other pharmaceuticals

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Taking the glucose solution with a concentration of 30% as raw material, taking Candida lipolytica as the fermentation strain, and assisting with trace elements, carry out expanded cultivation on a shaking table, then ferment for 3 days at 25°C, and obtain a fermentation inoculum size of 5 % of the erythritol crude product, the erythritol crude product is decolorized by activated carbon, filtered through a membrane, and separated by a macroporous resin to obtain an erythritol solution with a content of 80%.

[0024] (2) According to the dosage ratio, 1 part of erythritol solution prepared in step (1) is placed in a three-necked flask as a raw material, and 4 parts of hydrogen gas is introduced at a gas flow rate of 0.3 L / min, and citric acid solution is added. Adjust the pH value of the system to 5, stir and react at 45°C for 8 hours, then add an alkaline solution to neutralize to neutralize the reaction to stop, finally extract, and distill under reduced pressure to...

Embodiment 2

[0026] (1) With the concentration of 50% glucose solution as raw material, with Candida lipolytica as the fermentation strain, and with the assistance of trace elements, expand the culture on a shaking table, then ferment for 5 days at 35°C, and obtain a fermentation inoculum size of 10 % of the erythritol crude product, the erythritol crude product is decolorized by active carbon, membrane filtration, macroporous resin separation to obtain a content of 92% erythritol solution.

[0027] (2) According to the dosage ratio, 1 part of erythritol solution prepared in step (1) is placed in a three-necked flask as a raw material, and 6 parts of hydrogen gas is introduced at a gas flow rate of 0.5 L / min, and hydrochloric acid aqueous solution is added to adjust The pH value of the system was 6, and the reaction was stirred at 55°C for 12 hours, then an alkaline solution was added to neutralize to neutralize to stop the reaction, and finally extracted and distilled under reduced pressur...

Embodiment 3

[0029] (1) With the concentration of 40% glucose solution as raw material, with Candida lipolytica as the fermentation strain, and with the assistance of trace elements, expand the culture on a shaking table, then ferment for 4 days at 30°C, and obtain a fermentation inoculum size of 7 % of the erythritol crude product, the erythritol crude product is decolorized by active carbon, membrane filtration, macroporous resin separation to obtain a content of 84% erythritol solution.

[0030] (2) According to the dosage ratio, 1 part of erythritol solution prepared in step (1) is placed in a three-necked flask as a raw material, and 5 parts of hydrogen are fed into 5 parts of hydrogen at a gas flow rate of 0.4L / min, and hydrochloric acid aqueous solution is added to adjust The pH value of the system was 5.1, stirred and reacted at 50°C for 10 h, then neutralized to neutral by adding an alkaline solution to stop the reaction, finally extracted, and distilled under reduced pressure to o...

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Abstract

The invention provides a method for preparing (S)-3-hydroxytetrahydrofuran based on erythritol microorganisms. The method is characterized by comprising the steps that 1, a glucose solution is used as a raw material, candida lipolytica is used as a fermentation strain, enlarged cultivation and fermentation are performed to obtain crude erythritol, and the crude erythritol is subjected to decoloration, filtration and separation to obtain an erythritol solution; 2, the erythritol solution prepared in the step 1 is used as a raw material and put in a three-mouth flask, hydrogen is led into the flask, an acid solution is added into the flask, the solution is mixed for a reaction, then an alkaline solution is added for neutralization until the solution is neutral, then the reaction is stopped, and finally extraction and reduced pressure distillation are performed to obtain (S)-3-hydroxytetrahydrofuran. (S)-3-hydroxytetrahydrofuran is prepared after erythritol and hydrogen are subjected to a polymerization reaction in the acid environment, multiple processes such as erythritol drying and curing are omitted, the steps are simplified, the preparation method is simple and effective, the reaction is mild, cost is low, and technological production is facilitated.

Description

Technical field: [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for preparing (S)-3-hydroxytetrahydrofuran based on erythritol microorganisms. Background technique: [0002] (S)-3-Hydroxytetrahydrofuran is an important intermediate used in the synthesis of the anti-AIDS drug Amprenavir. It can also be used in the synthesis of pesticides in fine organic chemicals. After introducing (S)-3-Hydroxytetrahydrofuran group , can significantly improve the herbicidal activity and selectivity of diphenyl ether herbicides. [0003] At present, some reports on the synthesis of (S)-3-hydroxytetrahydrofuran have appeared in China, such as asymmetric hydroboration or hydrosilation of dihydrofuran, asymmetric hydrogenation of 4-chloro-3-oxobutyrate -Reduction-intramolecular etherification, enzymatic resolution of 3-hydroxytetrahydrofuran racemate, etc., but the optical purity of the prepared product is not good. In addition, there is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/04C07D307/20C12R1/73
CPCC12P17/04C07D307/20
Inventor 胡海威丁靓闫永平郑辉严辉
Owner ITIC MEDCHEM CO LTD
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