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Preparation method of isopropyl-β-d-thiogalactoside

A technology of thiogalactoside and propylthioacetyl, which is applied in the field of preparation of isopropyl-β-D-thiogalactoside, can solve the problems of high cost, complicated operation and low yield, and achieve The operation is simple, the raw materials are easy to obtain, and the effect of improving the safety factor

Active Publication Date: 2016-07-27
济南尚博医药股份有限公司
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Problems solved by technology

[0005] In order to solve the present situation that the cost in the preparation of isopropyl-β-D-thiogalactoside in the above prior art is relatively high, the operation is relatively complicated, and the yield is relatively low, the present invention provides a two-step method A method for preparing isopropyl-β-D-thiogalactoside with simple operation and readily available raw materials

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  • Preparation method of isopropyl-β-d-thiogalactoside

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Embodiment 1

[0022] 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;

[0023] b) Add 0.765 mol of isopropyl thioacetylgalactose 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%.

[0024] 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 crystallized, filtered and dried.

[0025] The post-treatment i...

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Abstract

The invention relates to the field of sugar compounds, in particular to a method for preparing isopropyl-β-D-thiogalactoside. Acetic anhydride and a catalyst are added at room temperature, and galactose is added. After the reaction is completed, isopropyl mercaptan is added. After the reaction is completed, after-treatment is performed to obtain isopropylthioacetylgalactose. Add isopropyl thioacetylgalactose to methanol to dissolve, add sodium methoxide, add acetic acid to neutralize after the reaction is completed, and obtain isopropyl-β-D-thiogalactoside after post-processing. The method of the invention synthesizes isopropyl-β-D-thiogalactoside through a two-step reaction method, has simple operation, readily available raw materials, and saves operating costs and materials.

Description

technical field [0001] The invention relates to the field of sugar compounds, in particular to a preparation method of isopropyl-β-D-thiogalactoside. Background technique [0002] Isopropyl-β-D-thiogalactopyranoside, also known as IPTG, English name: Isopropylβ-D-1-Thiogalactopyranoside, CAS number: 367-93-1, molecular formula C 9 h 18 o 5 S, the structural formula is as follows: [0003] [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 hig...

Claims

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Application Information

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Patent Type & Authority Patents(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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