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Process for synthesizing 20(S)-ginsenoside Rh2

一种合成方法、人参皂苷的技术，应用在甾族化合物、有机化学等方向，能够解决得率低、难以分离、不适宜大规模工业化生产等问题，达到选择性高、成本低、反应原料便宜易得的效果

Inactive Publication Date: 2006-04-19
SHANGHAI JIADA INFORMATION TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • 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

[0040] Embodiment 1 monosubstituted protopanaxadiol

[0041] Synthesis of (A2)

[0042] (1) R' is benzoyl (Bz) (ie 12-benzoyl-protopanaxadiol)

[0043] Protopanaxadiol (A1) [prepared by the method of Chinese invention patent (patent application number: 200410018038.8)] 40g (0.087mol) was dissolved in pyridine (600ml), benzoyl chloride 44.51g (0.261mol) was added at 0°C, 25 Stir at ℃ overnight, TLC detection, the reaction is complete, add methanol to terminate the reaction, concentrate and dissolve with ethyl acetate, then wash with saturated NaCl water until neutral, and dry. After filtration, it was concentrated and purified by column chromatography [gradient elution: volume ratio of petroleum ether to ethyl acetate from 6:1 to 3:1] to obtain 41.07 g of compound (A2-1), with a yield of 84.3%, as determined by HPLC The purity is 93.63%.

[0044] The physicochemical data of compound (A2-1) are as follows:

[0045] 1 H NMR (300MHz, CDCl 3 ): δ7.99-7.37(m, 5H), 5.2(m, 1H)...

Embodiment 2

[0062] Example 2 Fully protected D-glucose Synthesis of (B2)

[0063] (1) R is benzoyl (i.e. 1,2,3,4,6-penta-O-benzoyl-D-glucose) D-glucose (150g, 0.833mol) dissolved in 1650ml anhydrous pyridine, 0°C Add benzoyl chloride 532.5ml (4.575mol), stir overnight at room temperature, thin-layer chromatography detection, after the reaction is complete, pour it into a large amount of water, soak until solidified, wash with water, and dry to obtain a white solid, namely compound (B2 -1) 552.3g, the yield is 94.9%, and the purity determined by HPLC is 97.21%. Its physicochemical data correspond to 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 synthesis method).

[0064](2) R is acetyl (ie 1,2,3,4,6-penta-O-acetyl-D-glucose)

[0065] Add D-glucose (50g, 28mmol) and anhydrous sodium acetate (25g) to acetic anhydride (350ml), heat to 150-160°C until the solid dissolves, then pour it int...

Embodiment 3

[0074] Example 3 Glucose-based donor Synthesis of (B3)

[0075] (1) R is benzoyl, X is OC(NH)CCl 3

[0076] a. 120 g (0.146 mol) of compound (B2-1) was dissolved in 600 ml of N, N-dimethylformamide, 20.6 ml (0.36 mol) of glacial acetic acid was added under stirring at room temperature, and 20.16 ml of hydrazine hydrate ( 0.36mol), stirred at room temperature. Thin-layer chromatography detection, the reaction is completed, and purified by column chromatography [gradient elution: the volume ratio of petroleum ether to ethyl acetate is from 5:1 to 3:1] to obtain the structural formula: The white solid was 66g, the yield was 64.97%, and the purity determined by HPLC was 95.89%. Its physicochemical data are consistent with literature values: Mikamo, Masatomo; Carbohydr.Res.-1989, 191, 150-153.

[0077] b. 59g (0.095mol) of the compound obtained in the previous step was added to 150ml of anhydrous dichloromethane and stirred to dissolve the solid. Under argon protection, 17....

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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 synthetic method of ginsenosides with biological activity, specifically 20(S)-ginsenoside Rh2, i.e. 20(S)-protopanaxadiol-3-O-β-D-glucopyran The synthetic method of 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 found, and ginsenosides can be divided into Protopanaxdiol-type Gisenosides, Protopanaxtriol-type Gisnosides and oleanolic acid saponins according to saponins. 20(S)-ginsenoside Rh2 belongs to protopanaxadiol saponins. [0004] Since Odashima in Japan reported in 1985 that ginsenoside Rh2 could induce differentiation of melanoma B16 cells (Odashima S et al. Cancer Res.45(6), 2781, 1985), it has aroused the interest of sc...

Claims

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Application Information

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Patent Type & Authority Patents(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 SHANGHAI JIADA INFORMATION TECH CO LTD
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