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Preparation technique of isopropyl-beta-D-thiogalactoside

A thiogalactoside and preparation technology, which is applied in the field of isopropyl-β-D-thiogalactoside preparation technology, achieves the effects of simple operation, easy availability of raw materials, and improved safety factor

Active Publication Date: 2014-04-02
济南尚博医药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] 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 status, the present invention provides a preparation process of isopropyl-β-D-thiogalactoside that adopts a two-step method, is simple to operate, and has easy-to-get raw materials

Method used

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Embodiment 1

[0025] a) Add 6mol acetic anhydride and 1mol zinc chloride at room temperature, add 1mol galactose in 12 batches at 5-10°C, add 1.1mol isopropyl mercaptan after the reaction is completed, and obtain 0.732mol isopropyl after the reaction is completed Thioacetylgalactose;

[0026] b) Add 0.732 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 0.715 mol of isopropyl-β-D- Thiogalactosides. The yield was 71.5%.

[0027] 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.

[0028] The post-treatment in step b is to...

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Abstract

The invention relates to the field of saccharide compounds, particularly a preparation technique of isopropyl-beta-D-thiogalactoside. The technique comprises the following steps: adding acetic anhydride and a catalyst at room temperature, and adding galactose; after the reaction finishes, adding isopropyl mercaptan; after the reaction finishes, carrying out after-treatment to obtain isopropyl thioacetyl galactose; dissolving the isopropyl thioacetyl galactose in methanol, and adding sodium methoxide; and after the reaction finishes, adding acetic acid for neutralization, and carrying out after-treatment to obtain the isopropyl-beta-D-thiogalactoside. The method synthesizes the isopropyl-beta-D-thiogalactoside by a two-step reaction process, is simple to operate and accessible in raw materials, and saves the operating cost and materials.

Description

[0001] technical field [0002] The invention relates to the field of sugar compounds, in particular to a preparation process 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. [0004] 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 the cost is higher. For example, patent: 201210553...

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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