Isopropyl-beta-D-thiogalactoside preparation method

A technology of thiogalactoside and propylthioacetyl, which is applied in the field of preparation of isopropyl-β-D-thiogalactoside, achieves easy availability of raw materials, improves safety factor, saves operating costs and materials. Effect

Active Publication Date: 2014-04-09
济南尚博医药股份有限公司
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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

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  • Isopropyl-beta-D-thiogalactoside preparation method

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Embodiment 1

[0026] a) Add 5.5mol acetic anhydride and 1mol aluminum trichloride at room temperature, add 1mol galactose in 9 batches at 5-10°C, add 1.1mol isopropyl mercaptan after the reaction is completed, and obtain 0.765mol isopropyl mercaptan after the reaction is completed Propylthioacetylgalactose;

[0027] 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%.

[0028] 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 solution crystallized, filtered and dried.

[0029] The post-t...

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Abstract

The invention relates to the field of sugar compounds, and concretely relates to an isopropyl-beta-D-thiogalactoside preparation method. The method comprises the following steps: adding acetic anhydride and a catalyst at room temperature, adding galactose, adding isopropyl mercaptan after the above reaction, and post-processing to obtain isopropyl thioacetylgalactosamine; and adding isopropyl thioacetylgalactosamine into methanol for dissolving, adding sodium methoxide, adding acetic acid after the above reaction to neutralize, and post-processing to obtain isopropyl-beta-D-thiogalactoside. The method allows isopropyl-beta-D-thiogalactoside to be synthesized through a two-step reaction process, and has the advantages of simple operation, easily available raw materials, and saving of the operation cost and materials.

Description

[0001] technical field [0002] The invention relates to the field of sugar compounds, in particular to a preparation method of 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 t...

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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