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A method for preparing isopropyl-β-d-thiogalactoside

A technology of thiogalactoside and propyl thioacetyl, which is applied in the field of preparing isopropyl-β-D-thiogalactoside, can solve the problems of high cost, complicated operation, low yield and the like, and achieves operation Simple, easy to obtain raw materials, and the effect of improving the safety factor

Active Publication Date: 2016-04-27
济南尚博医药股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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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

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 15

[0022] Example 15.5:1:1:1.1

[0023] 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;

[0024] 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%.

[0025] 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 cr...

Embodiment 25

[0027] Example 25.5:1.5:1:1.2

[0028] 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;

[0029] 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%.

[0030] 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 s...

Embodiment 36

[0032] Example 36:1.5:1:1.2

[0033] 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;

[0034] b) Add 0.774 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 0.756 mol of isopropyl-β-D- Thiogalactosides. The yield was 75.6%.

[0035] 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 c...

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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

technical field [0001] The invention relates to the field of sugar compounds, in particular to a method for preparing 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 high...

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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