Preparation method of p-methylphenyl-beta-D-thioacetylgalactoside

Abstract

The invention relates to the field of carbohydrates and particularly relates to a preparation method of p-methylphenyl-beta-D-thioacetylgalactoside. The preparation method comprises the steps of adding acetic anhydride and a catalyst at room temperature; adding D-galactose; after the reaction is ended, dropwise adding the reaction liquid into a thiocresol and methylene dichloride solution; after the reaction is ended, carrying out after-treatment to obtain p-methylphenyl-beta-D-thioacetylgalactoside. The method is used for synthesizing p-methylphenyl-beta-D-thioacetylgalactoside through one-step reaction, and is simple in operation, easy to obtain raw materials and capable of saving operation cost and materials.

Description

technical field

[0001] The invention relates to the technical field of sugar compound synthesis, in particular to a preparation method of p-tolyl-β-D-thioacetylgalactoside. Background technique

[0002] p-Tolyl-β-D-thioacetylgalactoside, English name: P-Tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside, molecular formula C 21 h 26 o 9 S, the structural formula is as follows:

[0003] ,

[0004] Sugar compounds are the main source of energy required by all organisms to maintain life activities. They are not only nutrients, but some also have special physiological activities. They are the most widely distributed and most abundant organic compounds in nature. As a kind of Special carbohydrate compounds are widely used in the field of biomedicine due to their unique physiological activities.

[0005] In the prior art, literature (Dasgupta Somnath, Mukhopadhyay Balaram, Rajput Vishal Kumar, et al. Journal of Carbohydrate Chemistry. 2007,26(2): 1054-1061) reported th...

Examples

Embodiment 1

[0025] Example 1 5.5:1:1:1.1:4.5

[0026] a) Add 5.5 mol of acetic anhydride and 1 mol of aluminum trichloride to the reactor at room temperature, add 1 mol of D-galactose at 50-55 °C under temperature control, and react for 2 hours. After the reaction is completed, add 1.1 mol of p-toluene into the reaction droplet In thiophenol and 4.5mol of dichloromethane solution, the temperature was controlled to react at 15-20 ° C for 2 hours, after completion, 0.904mol of p-tolyl-β-D-thioacetylgalactoside was obtained through post-treatment, and the yield was 90.4%, purity 99.78%.

[0027] In step a, post-processing is to add dropwise 10 mol of deionized water at 0-5°C and stir for 1 hour, extract the aqueous layer with 4 mol of dichloromethane, separate the organic phase and wash the organic phase three times with 8 mol of deionized water, and separate the organic phase. Concentrated, crystallized by adding a mixture of 1 mol tert-butyl methyl ether and 3 mol isohexane, filtered an...

Embodiment 2

[0028] Example 2 5.5:1.5:1:1.2:4.5

[0029] a) Add 5.5 mol of acetic anhydride and 1.5 mol of aluminum trichloride at room temperature, add 1 mol of D-galactose at 50-55 °C under temperature control, and react for 3 hours. After the reaction is completed, add 1.2 mol of p-toluenethiophenol and In 4.5 mol of dichloromethane solution, the temperature was controlled to react at 15-20 ° C for 3 hours, and after completion, 0.911 mol of p-tolyl-β-D-thioacetylgalactoside was obtained through post-treatment, and the yield was 91.1%, Purity 99.81%.

[0030] In step a, post-processing is to add dropwise 10 mol of deionized water at 0-5°C and stir for 1 hour, extract the aqueous layer with 4 mol of dichloromethane, separate the organic phase and wash the organic phase three times with 8 mol of deionized water, and separate the organic phase. Concentrated, crystallized by adding a mixture of 1 mol tert-butyl methyl ether and 3 mol isohexane, filtered and dried.

Embodiment 3

[0031] Example 3 6:1.5:1:1.3:5.0

[0032] a) Add 6 mol of acetic anhydride and 1.5 mol of aluminum trichloride at room temperature, add 1 mol of D-galactose at 50-55 °C under temperature control, and react for 2.5 hours. After the reaction is completed, add 1.3 mol of p-toluenethiophenol and 5.0 mol of dichloromethane solution, the temperature was controlled to react at 15-20 ° C for 4 hours, and after completion, 0.907 mol of p-tolyl-β-D-thioacetylgalactoside was obtained through post-treatment, with a yield of 90.7% and a purity of 90.7%. 99.76%.

[0033] In step a, the post-treatment is to add dropwise 8 mol of deionized water at 0-5°C and stir for 1 hour, extract the aqueous layer with 4 mol of dichloromethane, separate the organic phase and wash the organic phase three times with 8 mol of deionized water, and separate the organic phase. Concentrated, crystallized by adding a mixture of 1 mol tert-butyl methyl ether and 2 mol isohexane, filtered and dried.

technical field

[0001] The invention relates to the technical field of sugar compound synthesis, in particular to a preparation method of p-tolyl-β-D-thioacetylgalactoside. Background technique

[0002] p-Tolyl-β-D-thioacetylgalactoside, English name: P-Tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside, molecular formula C 21 h 26 o 9 S, the structural formula is as follows:

[0003] ,

[0004] Sugar compounds are the main source of energy required by all organisms to maintain life activities. They are not only nutrients, but some also have special physiological activities. They are the most widely distributed and most abundant organic compounds in nature. As a kind of Special carbohydrate compounds are widely used in the field of biomedicine due to their unique physiological activities.

[0005] In the prior art, literature (Dasgupta Somnath, Mukhopadhyay Balaram, Rajput Vishal Kumar, et al. Journal of Carbohydrate Chemistry. 2007,26(2): 1054-1061) reported th...

Examples

Embodiment 1

[0025] Example 1 5.5:1:1:1.1:4.5

[0026] a) Add 5.5 mol of acetic anhydride and 1 mol of aluminum trichloride to the reactor at room temperature, add 1 mol of D-galactose at 50-55 °C under temperature control, and react for 2 hours. After the reaction is completed, add 1.1 mol of p-toluene into the reaction droplet In thiophenol and 4.5mol of dichloromethane solution, the temperature was controlled to react at 15-20 ° C for 2 hours, after completion, 0.904mol of p-tolyl-β-D-thioacetylgalactoside was obtained through post-treatment, and the yield was 90.4%, purity 99.78%.

[0027] In step a, post-processing is to add dropwise 10 mol of deionized water at 0-5°C and stir for 1 hour, extract the aqueous layer with 4 mol of dichloromethane, separate the organic phase and wash the organic phase three times with 8 mol of deionized water, and separate the organic phase. Concentrated, crystallized by adding a mixture of 1 mol tert-butyl methyl ether and 3 mol isohexane, filtered an...

Embodiment 2

[0028] Example 2 5.5:1.5:1:1.2:4.5

[0029] a) Add 5.5 mol of acetic anhydride and 1.5 mol of aluminum trichloride at room temperature, add 1 mol of D-galactose at 50-55 °C under temperature control, and react for 3 hours. After the reaction is completed, add 1.2 mol of p-toluenethiophenol and In 4.5 mol of dichloromethane solution, the temperature was controlled to react at 15-20 ° C for 3 hours, and after completion, 0.911 mol of p-tolyl-β-D-thioacetylgalactoside was obtained through post-treatment, and the yield was 91.1%, Purity 99.81%.

[0030] In step a, post-processing is to add dropwise 10 mol of deionized water at 0-5°C and stir for 1 hour, extract the aqueous layer with 4 mol of dichloromethane, separate the organic phase and wash the organic phase three times with 8 mol of deionized water, and separate the organic phase. Concentrated, crystallized by adding a mixture of 1 mol tert-butyl methyl ether and 3 mol isohexane, filtered and dried.

Embodiment 3

[0031] Example 3 6:1.5:1:1.3:5.0

[0032] a) Add 6 mol of acetic anhydride and 1.5 mol of aluminum trichloride at room temperature, add 1 mol of D-galactose at 50-55 °C under temperature control, and react for 2.5 hours. After the reaction is completed, add 1.3 mol of p-toluenethiophenol and 5.0 mol of dichloromethane solution, the temperature was controlled to react at 15-20 ° C for 4 hours, and after completion, 0.907 mol of p-tolyl-β-D-thioacetylgalactoside was obtained through post-treatment, with a yield of 90.7% and a purity of 90.7%. 99.76%.

[0033] In step a, the post-treatment is to add dropwise 8 mol of deionized water at 0-5°C and stir for 1 hour, extract the aqueous layer with 4 mol of dichloromethane, separate the organic phase and wash the organic phase three times with 8 mol of deionized water, and separate the organic phase. Concentrated, crystallized by adding a mixture of 1 mol tert-butyl methyl ether and 2 mol isohexane, filtered and dried.

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