Synthetic method for improving ginsenoside M1 and iso-butyryl chloride mono-esterification selectivity

A technology of isobutyryl chloride monoester and ginsenoside, applied in the production of steroids, organic chemistry, bulk chemicals, etc., can solve the problems of difficult separation and purification, limited source of EM1, poor water solubility of series M1 derivatives, etc. The effect of separation and purification, optimization of selectivity, and improvement of yield

Inactive Publication Date: 2014-02-19
大连杰信生物科技有限公司
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  • Abstract
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Problems solved by technology

However, EM1 has limited sources and is difficult to separate and purify
However, the seri

Method used

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  • Synthetic method for improving ginsenoside M1 and iso-butyryl chloride mono-esterification selectivity
  • Synthetic method for improving ginsenoside M1 and iso-butyryl chloride mono-esterification selectivity

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Embodiment 1

[0029] 1. Synthesis of monoetherification of ginsenoside M1 with tert-butyldimethylsilyl chloride

[0030] 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. Column chromatography purification

[0031] Procedure: amount of silica gel, 5 g; mobile phase, methanol / dichloromethane;

[0032] After gradient elution, the Rf value was 9 / 34 (8%MeOH / CH 2 Cl 2 ) of the product 100 mg

[0033] ...

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Abstract

The invention introduces a synthetic method for improving ginsenoside M1 and iso-butyryl chloride mono-esterification selectivity. Firstly, No.6 hydroxy of glycosyl of ginsenoside M1 is protected by using tert-butyldimethylsilyl chloride through esterification, and is subjected to mono-esterification reaction with equivalent iso-butyryl chloride in the ice-water bath under the nitrogen protection with dichloromethane as a solvent and triethylamine as an acid applying agent under the DMAP (4-dimethylamino-pyridine) catalysis; finally, a silicon protecting group is removed by using tetrabutylammonium fluoride.

Description

technical field [0001] It belongs to the field of traditional Chinese medicine preparations. The invention relates to the chlorosilane protection reaction of ginsenoside M1. 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 objects. 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 Compou...

Claims

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Application Information

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IPC IPC(8): C07J17/00
CPCY02P20/55
Inventor 弓晓杰肖景楠陈丽荣徐斐
Owner 大连杰信生物科技有限公司
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