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Method for preparing isopropyl-beta-D-thiogalactoside

A technology of thiogalactoside and propylthioacetyl, which is applied in the field of preparation of isopropyl-β-D-thiogalactoside, which achieves the effect 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

[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-thiogalactoside

Examples

Experimental program
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Effect test

Embodiment 1

[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 crystallized, filtered and dried.

[0026] The post-treatment in step b is to concentrate to dryness, add 0.2 mol ethanol and 1.8 mol tert-butyl methyl ether for crystallization, filter and dry.

[0027] Example 2 5.5 : 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 12 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 me...

Embodiment 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 solution crystallized, filtered and dried.

[0031] The post-treatment in step b is to concentrate to dryness, add 0.2 mol ethanol and 1.8 mol tert-butyl methyl ether for crystallization, filter and dry.

[0032] Example 3 6:1.5: 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 12 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 isopropylthioacetylgalactose to 10 mol of methanol to di...

Embodiment 3

[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 crystallized, filtered and dried.

[0036] The post-treatment in step b is to concentrate to dryness, add 0.2 mol ethanol and 1.8 mol tert-butyl methyl ether for crystallization, filter and dry.

[0037] Example 4 6 : 1 : 1: 1.1

[0038] 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;

[0039] b) Add 0.732 mol of isopropylthioacetylgalactose to 10 mol of methanol to dissolve, add 0.01 mol of sodium methoxide, ad...

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Abstract

The invention relates to the field of saccharide compounds, particularly a method for preparing isopropyl-beta-D-thiogalactoside. The method 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 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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