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Synthetic method for isopropyl-beta-D-thiogalactoside

A technology of thiogalactoside and synthesis method, which is applied in the synthesis field of isopropyl-β-D thiogalactoside, can solve the problems of toxicity, unsuitability for industrial production, low yield and the like, and achieves broad market prospects , easy operation, high yield effect

Inactive Publication Date: 2013-05-08
JIANGXI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The defect of this method is: the use of isopropyl mercaptan has an unpleasant smell and is toxic; in addition, an isomer impurity of IPTG will be produced while generating the key intermediate isopropyl-β-D thioacetylgalactoside , which leads to difficulties in the separation and purification of IPTG, and the yield is low. It is only suitable for laboratory synthesis and not suitable for industrial production.

Method used

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  • Synthetic method for isopropyl-beta-D-thiogalactoside
  • Synthetic method for isopropyl-beta-D-thiogalactoside
  • Synthetic method for isopropyl-beta-D-thiogalactoside

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] step one:

[0033] Add 23.4g (60mmol) pentaacetylgalactose and 120ml dichloromethane into a 500ml round flask, stir to dissolve, then add 9.12g (120mmol) thiourea to the system, stir thoroughly for 5min, then add boron trifluoride ether Solution 29.4ml (240mmol), stirred at room temperature for twelve hours, a white solid precipitated in the system, followed by TLC to detect the reaction, after the reaction was complete, filtered to obtain a white solid, recrystallized with acetone and petroleum ether to obtain pure S- Tetraacetylgalactose isothiouronium fluoride salt 24.5 grams, the yield is 96%.

[0034] Step two:

[0035] Add 17.1 grams (90 mmol) of sodium metabisulfite, 150 ml of dichloromethane and 150 ml of water into a 500 ml round bottom flask, stir well and add 24.5 grams (57 mmol) of S-tetraacetylgalactose isothiourea fluoride salt, and heat to reflux , reacted for 6-7h, tracked the reaction with TLC (petroleum ether / ethyl acetate=1:1), after the reaction wa...

Embodiment 2

[0041] step one:

[0042] Add 23.4g (60mmol) pentaacetylgalactose and 120ml dichloromethane into a 500ml round flask, stir to dissolve, then add 11.4g (150mmol) thiourea to the system, stir thoroughly for 5min, then add boron trifluoride ether Solution 29.4ml (240mmol), stirred at room temperature for twelve hours, a white solid precipitated in the system, followed by TLC to detect the reaction, after the reaction was complete, filtered to obtain a white solid, recrystallized with acetone and petroleum ether to obtain pure S- Tetraacetylgalactose isothiourea fluoride salt 25.6 grams, yield is 97%.

[0043] Step two:

[0044] Add 19.1 grams (100 mmol) of sodium metabisulfite, 150 ml of dichloromethane and 150 ml of water into a 500 ml round bottom flask, stir well and add 25.6 grams (58 mmol) of S-tetraacetylgalactose isothiuronium fluoride, and heat to reflux , reacted for 6-7h, tracked the reaction with TLC (petroleum ether / ethyl acetate = 1:1), after the reaction was compl...

Embodiment 3

[0050] step one:

[0051] Add 23.4g (60mmol) pentaacetylgalactose and 120ml dichloromethane into a 500ml round flask, stir to dissolve, then add 11.4g (150mmol) thiourea to the system, stir thoroughly for 5min, then add boron trifluoride ether Solution 14.9ml (120mmol), stirred at room temperature for 12 hours, a white solid was precipitated, and the reaction was tracked and detected by TLC. After the reaction was complete, the white solid was obtained by filtration and recrystallized to obtain pure S-tetraacetylgalactose isothio Urea fluoride salt 19.0 grams, yield is 74%.

[0052] Step two:

[0053] Add 10.0 grams (50 mmol) of sodium metabisulfite, 150 ml of dichloromethane and 150 ml of water into a 500 ml round bottom flask, stir well and add 19.0 grams (44 mmol) of S-tetraacetylgalactose isothiuronium fluoride salt, and heat to reflux , reacted for 6-7h, tracked the reaction with TLC (petroleum ether / ethyl acetate = 1:1), after the reaction was completed, cooled to room t...

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Abstract

The invention provides a synthetic method for isopropyl-beta-D-thiogalactoside, namely, the synthetic method for IPTG. The synthetic method comprises the following steps of reacting 5-acetylgalactosamine as a raw material with thiourea so as to obtain acetyl S-galactose isothiourea fluoro salt, then reacting with pyrosufite so as to obtain acetyl S-galactose, reacting with isopropyl bromide, and finally carrying out deacetylate so as to obtain the target compound isopropyl-beta-D-thiogalactoside. In the whole reaction process, 5-acetylgalactosamine and isopropyl bromide are taken as the main raw materials, and isopropyl mercaptan which smells bad and has toxicity is not needed, so that harm to human body health and environment is avoided effectively; and furthermore, the synthetic method has the advantages of simple and convenient operation, high yield, high purity and the like, and is applicable to industrial production.

Description

technical field [0001] The invention relates to a chemical synthesis method, in particular to a synthesis method of isopropyl-β-D thiogalactoside. technical background [0002] Isopropyl-beta-D-thiogalactopyranoside (IPTG for short). IPTG is an activity-inducing substance of β-galactosidase. When the vector DNA of pUC series (or other vector DNA with lacZ gene) is transformed into lacZ-deficient cells, or transfected with the vector DNA of M13 phage, if X-Gal and IPTG are added to the plate medium , due to the α-complementarity of β-galactosidase, gene recombinants can be conveniently selected according to whether white colonies (or phage plaques) appear. In addition, it can also be used as an expression inducer of expression vectors with promoters such as lac or tac. Due to the difficulty in synthesizing the substance, the substance mainly depends on imports, and the price is high. Therefore, low-cost synthesis of this substance has certain market prospects. [0003]...

Claims

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Application Information

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IPC IPC(8): C07H15/14C07H1/00
Inventor 陈军民原唐军张祎敏章荣立
Owner JIANGXI NORMAL UNIVERSITY
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