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Method for preparing isopropyl-beta-D-isopropylthiogalactoside

A technology of thiogalactoside and propylthioacetyl, applied in the field of preparation of isopropyl-β-D-thiogalactoside, to achieve the effect of saving operating costs and materials, simple operation, and easy-to-obtain raw materials

Active Publication Date: 2014-03-26
济南尚博医药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the above prior art in the preparation of isopropyl-β-D-thiogalactoside, the cost is relatively high, the operation is complicated, and the yield Relatively low current situation, the present invention provides a method for preparing isopropyl-β-D-thiogalactoside using a two-step method, simple operation, and easy-to-obtain raw materials

Method used

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  • Method for preparing isopropyl-beta-D-isopropylthiogalactoside
  • Method for preparing isopropyl-beta-D-isopropylthiogalactoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 5.5 : 1 : 1: 1.1

[0027] a) Add 5.5 mol of acetic anhydride and 1 mol of aluminum trichloride at room temperature, add 1 mol of galactose in 10 batches at 5-10°C, add 1.1 mol of isopropyl mercaptan after the reaction is completed, and obtain 0.765 mol of isopropyl mercaptan after the reaction is completed Propylthioacetylgalactose;

[0028] b) Add 0.765 mol of isopropylthioacetylgalactose to 10 mol of methanol to dissolve, add 0.01 mol of sodium methoxide, add 0.01 mol of acetic acid to neutralize after the reaction is completed, and obtain 0.743 mol of isopropyl-β-D- Thiogalactosides. The yield was 74.3%.

[0029] The post-treatment in step a is to dropwise add 10 mol of water at 0-5°C and stir for 2 hours, extract the aqueous layer with 5 mol of dichloromethane, separate the organic phase and wash the organic phase with 10 mol of water three times, separate the organic phase and concentrate, add 1mol tert-butyl methyl ether and 2mol isohexane mixed sol...

Embodiment 2

[0031] Example 2 5.5 : 1.5 : 1: 1.2

[0032] a) Add 5.5 mol of acetic anhydride and 1.5 mol of aluminum trichloride at room temperature, add 1 mol of galactose in 10 batches at 5-10 ° C, after the reaction is completed, add 1.2 mol of isopropyl mercaptan, after the reaction is completed, 0.771 mol is obtained after post-treatment Isopropylthioacetylgalactose;

[0033] b) Add 0.771 mol of isopropylthioacetylgalactose to 10 mol of methanol to dissolve, add 0.01 mol of sodium methoxide, add 0.01 mol of acetic acid to neutralize after the reaction is completed, and obtain 0.752 mol of isopropyl-β-D- Thiogalactosides. The yield was 75.2%.

[0034] The post-treatment in step a is to dropwise add 10 mol of water at 0-5°C and stir for 2 hours, extract the aqueous layer with 5 mol of dichloromethane, separate the organic phase and wash the organic phase with 10 mol of water three times, separate the organic phase and concentrate, add 1mol tert-butyl methyl ether and 2mol isohexane...

Embodiment 3

[0036] Example 3 6:1.5: 1: 1.2

[0037] a) Add 6 mol of acetic anhydride and 1.5 mol of aluminum trichloride at room temperature, add 1 mol of galactose in 10 batches at 5-10°C, add 1.3 mol of isopropyl mercaptan after the reaction is completed, and obtain 0.774 mol of isopropyl mercaptan after the reaction is completed Propylthioacetylgalactose;

[0038] b) Add 0.774 mol of isopropylthioacetylgalactose to 10 mol of methanol to dissolve, add 0.01 mol of sodium methoxide, add 0.01 mol of acetic acid to neutralize after the reaction is completed, and obtain 0.756 mol of isopropyl-β-D- Thiogalactosides. The yield was 75.6%.

[0039] The post-treatment in step a is to drop 10mol of water at 0-5°C and stir for 2 hours, extract the aqueous layer with 5mol of dichloromethane, separate the organic phase and wash the organic phase with 10mol of water three times, separate the organic phase and concentrate, add 1mol tert-butyl methyl ether and 2mol isohexane mixed solution crystall...

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Abstract

The invention relates to the field of sugar compounds and in particular relates to a method for preparing isopropyl-beta-D-isopropylthiogalactoside. The method comprises the following steps: adding acetic anhydride and a catalyst at room temperature, adding galactose, adding isopropyl mercaptan after the reaction is ended, and performing aftertreatment to obtain isopropylthiogalactoside after the reaction is ended; adding the isopropylthiogalactoside into methanol for dissolving, adding sodium methoxide, adding acetic acid for neutralizing after the reaction is ended, and performing aftertreatment to obtain the isopropyl-beta-D-isopropylthiogalactoside. According to the method, the isopropyl-beta-D-isopropylthiogalactoside is synthesized through a two-step reaction method, the operation is simple, the raw materials are readily available, and the operating cost and materials are saved.

Description

[0001] technical field [0002] The invention relates to the field of sugar compounds, in particular to a method for preparing isopropyl-β-D-thiogalactoside. Background technique [0003] Isopropyl-β-D-thiogalactopyranoside, also known as IPTG, English name: Isopropyl β-D-1-Thiogalactopyranoside, CAS number: 367-93-1, molecular formula C 9 h 18 o 5 S, the structural formula is as follows: [0004] [0005] In the prior art, the reaction of galactose and acetic anhydride under the action of sodium acetate is generally used to prepare pentaacetylgalactose, and the pentaacetylgalactose is dissolved in a catalyst and reacted with isopropyl mercaptan to prepare tetraacetylisopropylthiosemi Lactose and tetraacetylisopropylthiogalactose are deacetylated by sodium methoxide to prepare isopropyl-β-D-thiogalactoside. This method first prepares pentaacetylgalactose, and then purifies it to cause a certain consumption of raw materials. The operation is more complicated and th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/14C07H1/00
Inventor 孟庆文孔令华张恩选张雷赵海峰索晨苏
Owner 济南尚博医药股份有限公司
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