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Synthesis method for increasing ginsenoside M1 and decanoylchloride monoesterification selectivity

A ginsenoside and selectivity technology, applied in the field of chlorosilane protection reaction, can solve the problems of poor water solubility, difficult separation and purification of series M1 derivatives, limited source of EM1, etc., and achieve easy separation and purification, optimized selectivity, and increased yield Effect

Inactive Publication Date: 2014-04-02
大连杰信生物科技有限公司
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Problems solved by technology

However, EM1 has limited sources and is difficult to separate and purify
However, the series of M1 derivatives obtained by chemical synthesis technology have poor water solubility

Method used

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  • Synthesis method for increasing ginsenoside M1 and decanoylchloride monoesterification selectivity
  • Synthesis method for increasing ginsenoside M1 and decanoylchloride monoesterification selectivity

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1 The monoetherification of ginsenoside M1 and tert-butyldimethylsilyl chloride is synthesized

[0027] Add 100 mg of ginsenoside M1 and 5 times the equivalent of tert-butyldimethylsilyl chloride to a 25 mL Shouliang bottle equipped with an electromagnetic stirrer, under nitrogen protection, add an appropriate amount of triethylamine to dissolve in an ice-water bath, and react for 10 After 1 min, it was raised to room temperature, and the reaction progress was monitored by thin-layer chromatography. After 24 h of reaction, saturated ammonium chloride solution was added to stop the reaction. via CH 2 Cl 2 (3×10 mL) extraction, Brine washed the organic phase, anhydrous Na 2 SO 4 Dry and concentrate the solvent.

[0028] Column chromatography purification process: silica gel amount, 6g; mobile phase, methanol / dichloromethane; the Rf value obtained after gradient elution was 9 / 34 (8%MeOH / CH 2 Cl 2 ) product 109 mg The product is a milky white solid, which...

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Abstract

The present invention provides a synthesis method for increasing ginsenoside M1 and decanoylchloride monoesterification selectivity. According to the synthesis method, the hydroxyl at the site 6 of the ginsenoside M1 glycoside group is protected by using tert-butyldimethylsilyl chloride through an etherification manner, the obtained material and equivalent decanoylchloride are subjected to a monoesterification reaction in an ice water bath under nitrogen protection by adopting dichloromethane as a solvent and adopting triethylamine as an acid binding agent under a DMAP (4-dimethylaminopyridine) catalysis condition, and finally tetrabutylammonium fluoride is adopted to remove the silicon-protected group to obtain the product of the monoesterification reaction of the tert-butyldimethyl siloxane of the ginsenoside M1 and the decanoylchloride.

Description

technical field [0001] The invention relates to the chlorosilane protection reaction of ginsenoside M1 and belongs to the field of traditional Chinese medicine chemistry. Background technique [0002] Ginseng has anti-aging, anti-inflammatory, anti-allergic, hypoglycemic, repairing nerve damage and liver protection effects. Studies in recent years have shown that ginsenosides have anti-tumor effects, and most of them are based on Rg 3 、Rh 1 、Rh 2 etc. as the main research object. They have shown significant effects in promoting tumor cell apoptosis and tumor cell differentiation. Ginsenosides with different structures have different antitumor activities, and the antitumor activity of diol-type ginsenosides is significantly stronger than that of triol-type ginsenosides. With the in-depth study of saponin pharmacokinetics, it is found that the real anti-tumor effect is the secondary metabolite Compound K in animals, also known as ginsenoside M1, and ginsenoside Compound K ...

Claims

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Application Information

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IPC IPC(8): C07J17/00
Inventor 弓晓杰陈丽荣陆俊霞
Owner 大连杰信生物科技有限公司
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