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Method for synthesizing isopropyl-beta-D-thiogalactoside

A technology of thiogalactoside and thiogalactoside, which is applied in the field of synthesis of isopropyl-β-D-thiogalactoside, can solve the problems of fire-prone handling workload and environmental burden, and achieve process safety The effect of convenience and cheap raw materials

Inactive Publication Date: 2013-03-27
BEIJING LEADMAN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is to overcome the defects of easy fire or post-processing workload and large environmental burden in the existing synthetic method of isopropyl-β-D-thiogalactoside, and provide a new Synthetic method of isopropyl-β-D-thiogalactoside

Method used

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  • Method for synthesizing isopropyl-beta-D-thiogalactoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1 Preparation of isopropyl-β-D-thiogalactoside

[0015] Preparation of penta-O-acetyl-β-D-galactose

[0016] 1. Add 125 ml of acetic anhydride and 20 g of anhydrous sodium acetate into a 500 ml reaction flask, slowly heat to reflux to dissolve the solid completely, and then carefully add 25 g of D-galactose in batches. After the addition was complete, the reaction mixture was refluxed for an additional 120 minutes. Afterwards, the reaction solution was poured into 300 ml ice-water mixture and stirred vigorously for 30 minutes, and a khaki solid precipitated out. Filter, wash the filter cake with water 2-3 times, and dry below 70°C. The obtained 37.9 g of penta-O-acetyl-β-D-galactose was recrystallized with ethanol as a solvent, and dried to obtain 31.1 g of pure penta-O-acetyl-β-D-galactose as a colorless solid , the yield is about 57%.

[0017] 2. Add 150 ml of acetic anhydride and 20 g of anhydrous sodium acetate into a 500 ml reaction flask, slowly heat t...

Embodiment 2

[0023] Example 2 Preparation of isopropyl-β-D-thiogalactoside

[0024] Preparation of penta-O-acetyl-β-D-galactose

[0025]1. Add 125 ml of acetic anhydride and 20 g of anhydrous sodium acetate into a 500 ml reaction flask, slowly heat to reflux to dissolve the solid completely, and then carefully add 25 g of D-galactose in batches. After the addition was complete, the reaction mixture was refluxed for an additional 140 minutes. Afterwards, the reaction solution was poured into 300 ml ice-water mixture and stirred vigorously for 35 minutes, and a khaki solid precipitated out. Filter, wash the filter cake with water 2-3 times, and dry below 70°C. The obtained 37.9 g of penta-O-acetyl-β-D-galactose was recrystallized with ethanol as a solvent, and dried to obtain 31.1 g of pure penta-O-acetyl-β-D-galactose as a colorless solid , the yield is about 58%.

[0026] 2. Add 150 ml of acetic anhydride and 20 g of anhydrous sodium acetate into a 500 ml reaction flask, slowly heat to...

Embodiment 3

[0032] Example 3 Preparation of isopropyl-β-D-thiogalactoside

[0033] Preparation of penta-O-acetyl-β-D-galactose

[0034] 1. Add 125 ml of acetic anhydride and 20 g of anhydrous sodium acetate into a 500 ml reaction flask, slowly heat to reflux to dissolve the solid completely, and then carefully add 25 g of D-galactose in batches. After the addition was complete, the reaction mixture was refluxed for an additional 120 minutes. Afterwards, the reaction solution was poured into 300 ml ice-water mixture and stirred vigorously for 30 minutes, and a khaki solid precipitated out. Filter, wash the filter cake with water 2-3 times, and dry below 70°C. The obtained 37.9 g of penta-O-acetyl-β-D-galactose was recrystallized with ethanol as a solvent, and dried to obtain 31.1 g of pure penta-O-acetyl-β-D-galactose as a colorless solid , the yield is about 57%.

[0035] 2. Add 150 ml of acetic anhydride and 20 g of anhydrous sodium acetate into a 500 ml reaction flask, slowly heat t...

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Abstract

The invention discloses a method for synthesizing isopropyl-beta-D-thiogalactoside. The method comprises the steps of (1) carrying out acetylation on D-galactose and acetyloxide to prepare quinary-acetyl-beta-D-galactose; (2) carrying out catalytic reaction on the quinary-acetyl-beta-D-galactose and 2-propyl sulfhydrate to prepare 2,3,4,6-tetra-O-acetyl-1-isopropyl-beta-D-thiogalactoside; and (3) removing four acetyl protecting groups of 2,3,4,6-tetra-O-acetyl-1-isopropyl-beta-D-thiogalactoside to obtain isopropyl-beta-D-thiogalactoside, wherein the catalyst in the step (2) is anhydrous aluminum trichloride. Anhydrous aluminum trichloride is adopted as the catalyst; reaction of production of thioglycoside is finished at normal temperature; the material is cheap and easy to get; and the process is safe and convenient to operate.

Description

technical field [0001] The invention relates to a method for synthesizing an inducer, in particular to a method for chemically synthesizing isopropyl-β-D-thiogalactoside, and belongs to the field of synthesis of isopropyl-β-D-thiogalactoside. Background technique [0002] Isopropyl-β-D-thiogalactoside is an excellent inducer, which is not easily metabolized by bacteria and can induce the expression of foreign genes. For prokaryotic expression system, isopropyl-β-D-thiogalactose can increase the expression level. In the presence of isopropyl-β-D-thiogalactoside, the prokaryotic expressed product is stable, easy to identify and easy to purify. Therefore, isopropyl-β-D-thiogalactoside is widely used in the field of biomedicine. Establishing a convenient synthetic method is an important aspect of isopropyl-β-D-thiogalactoside research. As a glucosinolate compound, isopropyl-β-D-thiogalactoside can be synthesized through three steps of chemical reaction. The first step is to ...

Claims

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Application Information

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IPC IPC(8): C07H15/14C07H1/00
CPCY02P20/55
Inventor 不公告发明人
Owner BEIJING LEADMAN BIOCHEM
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