Process for synthesizing 20(S)-ginsenoside Rh2

A synthesis method and technology of ginsenosides are applied in the directions of steroids, organic chemistry, etc., can solve the problems of low yield, difficult separation, unsuitable for large-scale industrial production, etc., and achieve high selectivity, low cost, and cheap reaction raw materials. easy-to-get effect

Inactive Publication Date: 2005-03-02
上海嘉达信息科技有限公司
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0023] In this method, since the 12-position and 20-position hydroxyl groups of protopanaxadiol are not protected, it is easy to be mono-substituted and multi-substituted by glucosyl groups, and what is obtained is 3-position, 12-position and 20-position glucosyl-single-substituted protoginseng The mixture of five products of diol and 3-position, 12-position, 3-position and 20-glucosyl disubstituted protopanaxadiol (wherein the 3-glucosyl monosubstituted protopanaxadiol content is only 27%), resulting in target The product 20(S)-ginsenoside Rh2 is difficult to separate and the yield is very low
[0024] The preparation methods reported in the above literature all have defects of one kind or another in terms of reaction conditions, yield, cost or stereoselectivity of reaction products, and are not suitable for large-scale industrial production.

Method used

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  • Process for synthesizing 20(S)-ginsenoside Rh2
  • Process for synthesizing 20(S)-ginsenoside Rh2
  • Process for synthesizing 20(S)-ginsenoside Rh2

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Monosubstituted protopanaxadiol Synthesis of (A2)

[0039] (1) R' is benzoyl (Bz) (ie 12-benzoyl-protopanaxadiol)

[0040] Protopanaxadiol (A1) [prepared by the Chinese invention patent (patent application number: 200410018038.8)] 40g (0.087mol) was dissolved in pyridine (600ml), 44.51g (0.261mol) of benzoyl chloride was added at 0°C, 25 Stir at ℃ overnight, check by thin layer chromatography, the reaction is complete, add methanol to stop the reaction, dissolve in ethyl acetate after concentration, wash with saturated NaCl aqueous solution until neutral, and dry. After filtration, concentrated, purified by column chromatography [gradient elution: volume ratio of petroleum ether and ethyl acetate from 6:1 to 3:1] to obtain compound (A2-1) 41.07g, yield 84.3%, determined by HPLC The purity was 93.63%.

[0041] The physicochemical data of compound (A2-1) are as follows:

[0042] 1 H NMR (300MHz, CDCl 3 ): δ7.99-7.37(m, 5H), 5.2(m, 1H), 5.13(t, 1H), 3.9(dd...

Embodiment 2

[0059] Example 2 Fully protected D-glucose Synthesis of (B2)

[0060] (1) R is benzoyl (ie 1,2,3,4,6-penta-O-benzoyl-D-glucose)

[0061] D-glucose (150g, 0.833mol) was dissolved in 1650ml of anhydrous pyridine, 532.5ml (4.575mol) of benzoyl chloride was added at 0°C, stirred at room temperature overnight, detected by thin layer chromatography, after the reaction was complete, poured into a large amount of soaked in water until solidified, washed with water, and dried to obtain a white solid, that is, compound (B2-1) 552.3 g with a yield of 94.9% and a purity of 97.21% determined by HPLC. The physicochemical data are in agreement with literature values: Eagle, Andrew J.; et al, J. Chem. Res., 1993, 10, 2663-2679. (Refer to R.K.Ness, et al, J.Amer.Chem.Soc., 1951, 296-299 for the synthetic method).

[0062](2) R is an acetyl group (ie 1,2,3,4,6-penta-O-acetyl-D-glucose)

[0063] D-glucose (50g, 28mmol), anhydrous sodium acetate (25g) were added with acetic anhydride (350ml)...

Embodiment 3

[0073] Example 3 Glucose based donor Synthesis of (B3)

[0074] (1) R is benzoyl, X is OC(NH)CCl 3

[0075] a. Compound (B2-1) 120g (0.146mol) was dissolved in 600ml N,N-dimethylformamide, 20.6ml (0.36mol) of glacial acetic acid was added under stirring at room temperature, and 20.16ml of hydrazine hydrate was added dropwise at 0°C ( 0.36 mol), stirring at room temperature. TLC detection, the reaction was completed, purified by column chromatography [gradient elution: the volume ratio of petroleum ether and ethyl acetate from 5:1 to 3:1] to obtain the structural formula: The white solid was 66 g, the yield was 64.97%, and the purity determined by HPLC was 95.89%. Its physicochemical data agree with literature values: Mikamo, Masatomo; Carbohydr. Res., 1989, 191, 150-153.

[0076] b. 59 g (0.095 mol) of the compound obtained in the previous step was added with 150 ml of anhydrous dichloromethane and stirred to dissolve the solid. Under argon protection, 17.37 ml (0.171 ...

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Abstract

The synthesis process of 20(S)-ginsenoside Rh2, or 20(S)-protopanoxadiol-3-O-beta-D- pyranoheteroside, includes first selectively protecting protopanoxadiol to obtain substituted protopanoxadiol, the subsequent reaction between the substituted protopanoxadiol and glucosyl donor under the catalysis of Lewis acid to eliminate protecting radical, and separation and purification to obtain 20(S)-ginsenoside Rh2. The said process has mild reaction condition, low cost, high stereo selectivity on reaction product, high yield and high purity, and is suitable for industrial production.

Description

technical field [0001] The present invention relates to a kind of synthetic method of ginsenoside with biological activity, specifically 20(S)-ginsenoside Rh2, namely 20(S)-protopanaxadiol-3-O-β-D-glucopyran Synthesis of the glycoside [20(S)-protopanaxdiol-3-O-β-D-glucopyranoside, whose structure is shown below]. [0002] Background technique [0003] Ginseng is recognized as a valuable traditional Chinese medicine for nourishing and strengthening the body. The main active ingredient of ginseng is saponin. There are 34 kinds of ginsenosides that have been discovered. Ginsenosides can be divided into protopanaxdiol-type gisenosides, protopanaxtriol-type gisnosides and oleanolic acid saponins according to sapogenin. 20(S)-ginsenoside Rh2 belongs to protopanaxadiol saponins. [0004] Since Japan's Odashima reported in 1985 that ginsenoside Rh2 can induce differentiation of melanoma B16 cells (Odashima S et al. Cancer Res. 45(6), 2781, 1985), it has attracted the interest o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/00C07J17/00
Inventor 惠永正杨志奇刘俊耀滕继军谢慧琴张捷
Owner 上海嘉达信息科技有限公司
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