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Method for synthesizing isopropyl-beta-D-thiogalactoside (IPTG)

A technology of thiogalactoside and a synthesis method, which is applied in the field of synthesis of isopropyl-β-D-thiogalactoside, can solve the problems of increased production cost, long steps and routes, and can avoid environmental hazards, The effect of low cost and high yield

Active Publication Date: 2018-11-06
丹江口市御景生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is obviously superior to the aforementioned method in terms of environmental protection, but the step route is relatively long, which increases the production cost

Method used

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  • Method for synthesizing isopropyl-beta-D-thiogalactoside (IPTG)
  • Method for synthesizing isopropyl-beta-D-thiogalactoside (IPTG)

Examples

Experimental program
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Effect test

Embodiment 1

[0025] The first step, β-D-galactose pentaacetate (390.3 grams, 1mol) was dissolved in dichloromethane (1L), added boron trifluoride ether (5.7 grams, 0.04mol) and ethyl xanthic acid Potassium (160.3 g, 1 mol) was reacted, stirred and reacted for 3 hours at -5 ° C, the reaction was completed, the reaction solution was washed twice, and the dichloromethane was dried with anhydrous sodium sulfate. Then, the dichloromethane was removed by rotary evaporation to obtain Tetraacetyl galactose ethyl xanthate 420 grams, yield 93%. m / z=453.10(M+1);

[0026] The second step, take the above-mentioned tetraacetylsemisugar ethyl xanthate (226 grams, 0.5mol) and 2-bromopropane (67.7 grams, 0.55mol) and potassium carbonate (83 grams, 0.6mol) and be dissolved in 2L methanol reaction at 50°C, after 4 hours, the reaction is complete, add concentrated hydrochloric acid to adjust the pH value to 5-7, remove the potassium bromide generated during the reaction by suction filtration, and then remove...

Embodiment 2

[0028] The first step, β-D-galactose pentaacetate (390.3 grams, 1mol) was dissolved in chloroform (1.5L), added boron trifluoride ether (7 grams, 0.05mol) and ethyl xanthogen Potassium chloride (192.4 g, 1.2 mol) was reacted, stirred and reacted at -8°C for 4 hours, the reaction was completed, the reaction solution was washed twice with water, and the chloroform was dried with anhydrous sodium sulfate, and then the chloroform was removed by rotary evaporation. 428 g of tetraacetyl galactosyl xanthate was obtained with a yield of 95%.

[0029] The second step, get the above-mentioned tetraacetylgalactose ethyl xanthate (226 grams, 0.5mol) and 2-bromopropane (74 grams, 0.6mol) and potassium carbonate (90 grams, 0.65mol) and be dissolved in 2L methanol , react at 60°C, after 5 hours, the reaction is complete, add concentrated hydrochloric acid to adjust the pH value to 5-7, remove the potassium bromide generated during the reaction by suction filtration, and then remove the metha...

Embodiment 3

[0031] In the first step, β-D-galactose pentaacetate (390.3 grams, 1mol) was dissolved in methylene chloride (2L), and zinc chloride (5.5 grams, 0.04mol) and sodium ethyl xanthate ( 158.6 grams, 1.1mol) reacted, stirred and reacted at -3°C for 3 hours, the reaction was completed, the reaction solution was washed twice with water, and the dichloromethane was dried with anhydrous sodium sulfate. Then, the dichloromethane was removed by rotary evaporation to obtain tetraacetyl 412 grams of galactose ethyl xanthate, yield 91%.

[0032] The second step, get the above-mentioned tetraacetylgalactose ethyl xanthate (226 grams, 0.5mol) and 2-bromopropane (74 grams, 0.6mol) and sodium carbonate (80 grams, 0.75mol) and be dissolved in 2L ethanol , react at 70°C, after 5 hours, the reaction is complete, add concentrated hydrochloric acid to adjust the pH value to 5-7, remove the potassium bromide generated during the reaction by suction filtration, and then remove ethanol by rotary evapor...

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Abstract

The invention provides a method for synthesizing isopropyl-beta-D-thiogalactoside (IPTG) and belongs to the technical field of organic synthesis. The method comprises the following steps: taking a compound beta-D-galactose pentaacetate as a raw material, and reacting with potassium ethyl xanthate in the presence of a catalyst so as to obtain tetraacetyl galactose ethyl xanthate; reacting with 2-bromopropane under an alkaline condition, so as to obtain the isopropyl-beta-D-thiogalactoside (IPTG). According to the synthetic method, the beta-D-galactose pentaacetate, potassium ethyl xanthate and2-bromopropane are taken as main raw materials, 2-mercaptopropane which is extremely unpleasant in smell, easy to diffuse and high in toxicity used in the original method is replaced, and the harm tothe environment is effectively avoided. The raw materials used in the method disclosed by the invention are readily available, the operating process is simple and convenient, the reaction condition ismild, and the method is safe, controllable and high in yield.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, in particular to a method for synthesizing isopropyl-β-D-thiogalactoside. Background technique [0002] Isopropyl-β-D-thiogalactoside (IPTG), molecular formula: C9H18O5S, molecular weight: 238.3, CAS: 367-93-1, structural formula as follows: [0003] [0004] Isopropyl-β-D-thiogalactoside (IPTG) is an activity-inducing substance of β-galactosidase, which induces the expression of foreign genes and is widely used in prokaryotic expression systems. It is a very strong inducer, which is not metabolized by bacteria and is very stable, and has been widely used in laboratories. But in the past, it was only limited to laboratory scientific research, and the demand has not been high. In recent years, the application of IPTG has gone out of laboratory research and into industrial production, especially in the production of amino acids. At present, in the production of industrial kiloton-le...

Claims

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Application Information

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IPC IPC(8): C07H15/14C07H1/00
CPCC07H1/00C07H15/14
Inventor 余书强
Owner 丹江口市御景生物医药有限公司
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