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Preparation method of tribenoside

A technology of tribenzyl glucoside and tribenzyl monosaccharide, which is applied in the field of preparation of tribenzyl glucoside, can solve the problems of difficult temperature control, harm to people and equipment, and easy generation of impurities, and achieves convenient operation, less impurities and mild reaction conditions. Effect

Inactive Publication Date: 2018-02-16
山东康曼生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction temperature of this method is relatively high, the exotherm is violent when adding potassium hydroxide, the temperature is not easy to control, and impurities are likely to be generated, and the introduction of a large amount of hydrochloric acid gas in industrial production is harmful to people and equipment, and an additional tail gas absorption device is required.

Method used

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  • Preparation method of tribenoside
  • Preparation method of tribenoside

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A kind of preparation method of tribenzyl glucoside of the present invention, comprises the steps:

[0030] (1) Add monoacetone glucose and phase transfer catalyst to benzyl chloride, add inorganic alkali solution A dropwise at 70°C under controlled temperature, and stir for 4 hours after the drop; the phase transfer catalyst is benzyl triethyl ammonium chloride. The inorganic base A is a combination of sodium hydroxide and potassium hydroxide. The ratio of monoacetone glucose, inorganic alkali solution A, phase transfer catalyst and benzyl chloride is 1: 3.0: 0.05: 6.0.

[0031] (2) Cool the reaction solution to 30°C, add organic solvent B for extraction, take the supernatant, wash 4 times with drinking water and 1 time with saturated saline, and distill the organic solvent B under reduced pressure; the organic solvent B is benzene.

[0032] (3) The above materials are distilled with a three-stage molecular equipment, the three-stage molecular equipment is a first-s...

Embodiment 2

[0038] The difference between embodiment 2 and embodiment 1 is: a kind of preparation method of tribenzyl glucoside of the present invention comprises the following steps:

[0039] (1) Add glucose monoacetone and a phase transfer catalyst to benzyl chloride, add inorganic alkali solution A dropwise at 75°C under control of the temperature, and stir for 5 hours after the drop; the phase transfer catalyst is tetrabutyl bromide A combination of two of ammonium chloride and tetrabutylammonium chloride. The inorganic base A is cesium hydroxide. The ratio of monoacetone glucose, inorganic alkali solution A, phase transfer catalyst and benzyl chloride is 1:5.0:0.01:3.0.

[0040] (2) Cool the reaction solution to 20°C, add organic solvent B for extraction, take the supernatant, wash 2 times with drinking water, 1.5 times with saturated saline, and distill the organic solvent B under reduced pressure; the organic solvent B is A combination of three of chloroform, carbon tetrachloride...

Embodiment 3

[0046] The difference between embodiment 3 and embodiment 1 is: a kind of preparation method of tribenzyl glucoside of the present invention, comprises the following steps:

[0047] (1) Add monoacetone glucose and phase transfer catalyst to benzyl chloride, add inorganic alkali solution A dropwise at 80°C under controlled temperature, and stir for 4.5 hours after the drop is completed; the phase transfer catalyst is tetrabutylsulfuric acid A combination of ammonium hydrogen and tetrabutylammonium bromide. The inorganic base A is a combination of lithium hydroxide and barium hydroxide. The ratio of monoacetone glucose, inorganic alkali solution A, phase transfer catalyst and benzyl chloride is 1: 4.0: 0.03: 7.0.

[0048] (2) Cool the reaction solution to 25°C, add organic solvent B for extraction, take the supernatant, wash 3 times with drinking water and 2 times with saturated saline, and distill the organic solvent B under reduced pressure; the organic solvent B is A combin...

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Abstract

The invention discloses a preparation method of tribenoside. The method comprises the following steps: adding monoacetone glucose and a phase transfer catalyst to benzyl chloride, controlling the reaction temperature of a system, adding an inorganic base solution dropwise to obtain a crude product of tribenzyl monoacetone glucose, performing three-stage molecular distillation for purification toobtain high-purity tribenzyl monoacetone glucose, and adding high-purity tribenzyl monoacetone glucose to ethanol hydrochloride to prepare tribenoside. The method has the advantages of simple and efficient synthesis process, reasonable process, high synthesis efficiency and high yield; reaction operation is simple and convenient, tribenoside contains fewer impurities and is higher in purity and content, operation is convenient, and the European pharmacopoeia standards can be met directly.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis and pharmacy, and in particular relates to a preparation method of tribenzyl glycoside. Background technique [0002] Tribenzyl glucoside is a hemorrhoid drug created by Ciba Company. It was developed in Japan with the introduction of technology from Takeda Pharmaceutical Company. It is mainly used as an anti-inflammatory drug and can also be used as a raw material for various anti-inflammatory drugs. It is suitable for bleeding and swelling of internal hemorrhoids. [0003] In the existing technology, glucose monoacetone is added to benzyl chloride, heated in an oil bath, and the temperature is controlled at 85-95°C. Slowly add potassium hydroxide solid under stirring, the reaction is exothermic, and the addition speed is controlled. After the reaction is completed, the temperature of the system is lowered, water and organic solvent are added dropwise and allowed to stand for stratif...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00C07H1/06
CPCC07H1/00C07H1/06C07H15/18
Inventor 孙继朋花卉孙晋宝胡自娟
Owner 山东康曼生物科技有限公司
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