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A method for preparing p-thiocresol-tetra-o-acetyl-β-d-galactose

A technology of thiocresol and acetyl group is applied in the field of preparation of p-thiocresol-tetra-O-acetyl-β-D-galactose, and can solve the problems of complicated operation, unpleasant smell, low synthesis rate, etc. problem, to achieve the effect of simple operation, improved yield and easy crystallization

Active Publication Date: 2016-08-17
济南尚博医药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this reaction avoids the defects of low synthesis rate and bad smell caused by direct synthesis with isopropyl mercaptan, the invention is cumbersome to operate and requires four steps of reaction to obtain the target product

Method used

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  • A method for preparing p-thiocresol-tetra-o-acetyl-β-d-galactose
  • A method for preparing p-thiocresol-tetra-o-acetyl-β-d-galactose
  • A method for preparing p-thiocresol-tetra-o-acetyl-β-d-galactose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] a. Separately cool 400ml acetone, 80g p-thiocresol and 100g bromo-tetra-O-acetyl-β-D-galactose to 0°C, dissolve p-thiocresol and bromo-cresol with 0°C acetone Tetra-O-acetyl-β-D-galactose and then mixed and stirred;

[0026] b. Add an alkaline aqueous solution of sodium hydroxide with a mass concentration of 20%, adjust the pH of the solution to 6, keep the temperature at 3°C, and stir for 60 minutes;

[0027] c. After the reaction is completed, dilute hydrochloric acid is added to neutralize the solution to pH=7.2;

[0028] d. Slowly add water at 40°C under stirring at -5°C until crystals are formed, stop adding water, continue stirring for 1 hour, centrifuge, and wash the crystals with a mixed solution of acetone and water with a volume ratio of 1:1;

[0029] e. After drying, crystals are obtained.

[0030] The quality of the crystal obtained by weighing in the present invention is 98.3g, and the calculated yield is 91.38%;

[0031] The present invention carries ou...

Embodiment 2

[0034] a. Separately cool 450ml acetone, 90g p-thiocresol and 100g bromo-tetra-O-acetyl-β-D-galactose to 5°C, dissolve p-thiocresol and bromo-cresol with 5°C acetone Tetra-O-acetyl-β-D-galactose and then mixed and stirred;

[0035] b. Add an alkaline aqueous solution of sodium hydroxide with a mass concentration of 30%, adjust the pH of the solution to 6.5, keep the temperature at 10°C, and stir for 30 minutes;

[0036] c. After the reaction is completed, dilute hydrochloric acid is added to neutralize the solution to pH=7.8;

[0037] d. Slowly add water at 58°C dropwise under stirring at 0°C until crystals are formed, stop adding water, continue stirring for 3 hours, centrifuge, and wash the crystals with a mixed solution of acetone and water with a volume ratio of 1:2;

[0038] e. After drying, crystals are obtained.

[0039] The quality of the crystal obtained by weighing in the present invention is 99.45g, and the calculated yield is 92.45%;

[0040] In the present inve...

Embodiment 3

[0043] a. Separately cool 500ml acetone, 110g p-thiocresol and 100g bromo-tetra-O-acetyl-β-D-galactose to 3°C, dissolve p-thiocresol and bromo-cresol with 3°C acetone Tetra-O-acetyl-β-D-galactose and then mixed and stirred;

[0044] b. Add an alkaline aqueous solution of sodium hydroxide with a mass concentration of 15%, adjust the pH of the solution to 6.8, keep the temperature at 5°C, and stir for 50 minutes;

[0045] c. After the reaction is completed, dilute hydrochloric acid is added to neutralize the solution to pH=7.5;

[0046] d. Under stirring, slowly add water at 52°C dropwise at 5°C until crystals are formed, stop adding water, continue stirring for 2 hours, centrifuge, and wash the crystals with a mixed solution of acetone and water with a volume ratio of 1:1;

[0047] e. After drying, crystals are obtained.

[0048] The quality of the crystal obtained by weighing in the present invention is 103.65g, and the calculated yield is 96.36%;

[0049] In the present in...

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Abstract

The present invention relates to the field of sugar compounds, in particular to a preparation method of p-thiocresol-tetra-O-acetyl-β-D-galactose, comprising the following steps: a. acetone, p-thiocresol and bromine Substitute-four-O-acetyl-β-D-galactose is cooled to 0-5°C separately, then mixed and stirred; b. Add alkaline aqueous solution, keep the temperature at 3-10°C, and stir for 30-60min; c. The reaction is completed Finally, add dilute acid to neutralize to pH=7‑8; d. Add water at 40‑60 °C at ‑5‑5 °C under stirring, after crystals are produced, stop adding water and continue stirring for 1‑3h, centrifuge, and wash the solid ; e, drying the resulting crystals is the product. The invention is easy to operate, the product is easy to crystallize, and the yield is increased to more than 97%.

Description

technical field [0001] The invention relates to the field of sugar compounds, in particular to a preparation method of p-thiocresol-tetra-O-acetyl-β-D-galactose. Background technique [0002] Chinese Patent Publication No. CN103087121A discloses a "synthetic method of isopropyl-β-D thiogalactoside", which uses pentaacetylgalactose as raw material and reacts with thiourea to obtain acetyl S-galactose Isothiouronium fluoride, followed by reaction with pyrosulfite to obtain acetyl S-galactose, then reacted with isopropyl bromide, and finally deacetylated to obtain the target compound isopropyl-β-D thiogalactoside. Although this reaction avoids the low synthesis rate caused by the direct synthesis with isopropyl mercaptan and the defects of bad smell, the invention is cumbersome to operate and requires four steps of reaction to obtain the target product. Contents of the invention [0003] The technical problem solved by the present invention is to provide a high yield, simple...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/203C07H1/00
Inventor 孟庆文张文岺王武宝
Owner 济南尚博医药股份有限公司