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Method for separating and purifying beta-end-group thio-glycoside compound

An end-group thioglycoside and purification method technology, which is applied in the field of separation and purification of beta-end-group thioglycoside compounds, can solve the problems of long separation time, complicated operation and the like, and achieve the effect that the separation and purification method is simple and quick.

Active Publication Date: 2013-10-09
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

When using column chromatography to separate β-terminal thioglycoside compounds, not only must a large amount of organic solvent be used, but also because the polarity difference between the two isomers is not large, the separation takes a long time and the operation is cumbersome

Method used

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  • Method for separating and purifying beta-end-group thio-glycoside compound
  • Method for separating and purifying beta-end-group thio-glycoside compound
  • Method for separating and purifying beta-end-group thio-glycoside compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of thioglycoside compounds with reference to the Chinese patent application number 201210114627:

[0037] a) Add 640ml of 33wt% acetic acid / HBr solution to 607g of acetylated fucose, stir to dissolve, react for about 1.5h, and test the reaction progress by TLC spot plate; the reaction is considered complete when the raw material point disappears; then add to the reaction solution Add 1.9L of dichloromethane, then add 5wt% Na 2 CO 3 863ml of the solution was used to neutralize the pH value to 7, and the organic phase was separated by stirring. The organic phase was dried with anhydrous sodium sulfate and then evaporated to dryness at 40°C to obtain bromoacetylated fucose with a theoretical yield of 645g.

[0038]b) Add 480g of bromoacetylated fucose to 2.5L of acetonitrile to dissolve it, and heat it to 70°C; slowly add 144.5g of thiourea to the reaction solution, and white flocs will form when the reflux begins; After adding thiourea, react for about 30 mi...

Embodiment 2

[0041] Dissolve 50 g of the crude thiofucoside compound obtained in Example 1 into 100 ml of dichloromethane, add 100 ml of an aqueous solution of copper sulfate with a mass fraction of 5%, stir at -20°C for 30 min, separate the organic phase by filtration, and heat to 40 degrees, dichloromethane was evaporated to obtain an oily product. Add 100ml of a mixture of methyl tert-butyl ether and isohexane (1:2 volume ratio of methyl tert-butyl ether and isohexane) to the oily product, and put the device containing the above product into ultrasonic vibration until all crystals are precipitated . Filtration and washing with isohexane gave 18.5 g of crystals with a purity of 98.5%, with a yield of 91%.

[0042] Experimental analysis was carried out on the obtained crystals, figure 1 It is the hydrogen nuclear magnetic resonance spectrum of the β-terminal thiofucoside compound, figure 2 It is the carbon nuclear magnetic resonance spectrum of the β-terminal thiofucoside compound, co...

Embodiment 3

[0044] Dissolve 100g of the crude thiofucoside compound obtained in Example 1 into 200ml of dichloromethane, add 200ml of copper sulfate solution with a mass fraction of 8%, stir at -15°C for 40min, separate the organic phase, and heat to 40 degree, dichloromethane was evaporated to obtain an oily product. Add 250ml of a mixture of methyl tert-butyl ether and isohexane (volume ratio 1:3) to the oily product, and put the device containing the above product into ultrasonic vibration until all crystals are precipitated. Filter and wash with isohexane to obtain 37.8 g of crystals with a purity of 98.2%, that is, β-terminal thioglycoside compounds, with a yield of 92.8%.

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Abstract

The invention provides a method for separating and purifying a beta-end-group thio-glycoside compound. The method comprises the following steps of: dissolving a crude thio-glycoside compound containing various isomers into a first organic solvent, adding an aqueous solution containing a divalent copper salt, stirring at the temperature between minus 20 DEG C and 0 DEG C, and filtering to obtain an organic phase; drying the organic phase by distilling, dissolving the dried organic phase into a second organic solvent, and shaking ultrasonically to obtain the beta-end-group thio-glycoside compound. Because the steric hindrance of the alpha-end-group isomer is low, the alpha-end-group isomer is easy to be subjected to complexation with a cupric ion to generate a flocculent precipitate in a low-temperature aqueous phase, and because the flocculent precipitate can be removed easily by filtering, the beta-end-group isomer can be left in the organic phase. After the beta-end-group isomer is shaken ultrasonically, the beta-end-group isomer can crystallize. The method provided by the invention is simple and convenient. In addition, the experimental result shows that the purity of the beta-end-group thio-glycoside compound obtained by adopting the method can be more than 95%, and the yield can be more than 85%.

Description

technical field [0001] The invention relates to the field of sugar compounds, in particular to a method for separating and purifying β-terminal thioglycoside compounds. Background technique [0002] Carbohydrates are a general term for a class of compounds that contain polyhydroxy aldehydes or polyhydroxy ketones and can generate polyhydroxy aldehydes or polyhydroxy ketones after hydrolysis. Carbohydrates are the most widely distributed and most abundant organic compounds in nature, one of the components of food, and the direct product of photosynthesis of green plants. Carbohydrates account for about 3 / 4 of biological substances in nature, and all of them contain carbs from bacteria to higher animals. At the same time, carbohydrate compounds are also the main source of energy required by organisms to maintain life activities, the basic raw materials for the synthesis of other compounds, and the main structural components of organisms. Therefore, carbohydrates are one of t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/14C07H1/06
Inventor 唐地源张文岺刘顶王恩华
Owner 济南尚博医药股份有限公司
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