Manufacturing method of glycyrrhizic acid and D-galacturonic acid glycyrrhizic acid and intermediate used thereby

A manufacturing method and compound technology, applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve problems such as complex procedures, low yield, and no reported synthesis method of galacturonic acid glycyrrhizic acid, etc., to achieve The effect of simple process

Pending Publication Date: 2018-07-03
TSUMURA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no synthesis method of galacturonic acid glycyrrhizic acid has been reported so far
In addition, some methods for synthesizing glycyrrhizic acid and its analogues have been proposed, but any method has complicated steps or low yields and is impractical (Patent Document 1, Non-Patent Documents 2 and 3)

Method used

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  • Manufacturing method of glycyrrhizic acid and D-galacturonic acid glycyrrhizic acid and intermediate used thereby
  • Manufacturing method of glycyrrhizic acid and D-galacturonic acid glycyrrhizic acid and intermediate used thereby
  • Manufacturing method of glycyrrhizic acid and D-galacturonic acid glycyrrhizic acid and intermediate used thereby

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Manufacture of Glycyrrhizic Acid Galacturonate:

[0080] (1-1) Synthesis of Benzyl Glycyrrhetinate

[0081]

[0082] Glycyrrhetinic acid (compound (1')), 4.74g, 10.1mmol) and sodium bicarbonate (3.39g, 40.4mmol) were dissolved in dimethylformamide (25ml), and benzyl bromide (3.60ml, 30.3 mmol), stirred at 80°C for 2 hours. After cooling to room temperature, water and ethyl acetate were added. The aqueous layer was extracted with hexane: ethyl acetate = 4:1, the organic layer was washed with saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the obtained filtrate was concentrated under reduced pressure. The obtained residue was purified by flash silica gel chromatography (hexane:ethyl acetate=5:1→3:1) to obtain the target compound (1-I) (MW560.81, 5.59g, 9.97 mmol) as a white powder ). The physicochemical properties of compound (1) are shown below.

[0083] 1 H-NMR (CDCl 3 ,600MHz)δ:0.69(1H,d,J=11.5Hz),0.73(3H,s),0.80...

Embodiment 2

[0137] Synthesis of glycyrrhizic acid;

[0138] (IVb) Glycosylation of Compound (3-I)

[0139]

[0140] Compound (3-I) (1.30 g, 1.31 mmol) produced in Example 1, and compound (4b-I) (phenyl 2,3,4,6-tetra-O-acetyl-1-sulfur N-iodosuccinimide (0.59 g, 2.62 mmol) was added to a solution of dichloromethane (50 ml) in substituted-β-D-glucopyranoside, 1.15 g, 2.61 mmol, and cooled to -60°C . A dichloromethane (1 ml) solution of trifluoromethanesulfonic acid (11.6 µl, 0.131 mmol) was added dropwise to the reaction solution over 10 minutes. Stirring was carried out while gradually raising the temperature to room temperature over 3.5 hours. Triethylamine was added to stop the reaction, and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution, aqueous sodium thiosulfate solution, water, saturated aqueous sodium bicarbonate solution and saturated brine, and dried over sodium sulfate. After removing sodium sulfat...

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Abstract

The invention discloses a manufacturing method of glycyrrhizic acid and D-galacturonic acid glycyrrhizic acid and an intermediate used thereby. The invention provides a synthesis method that is capable of simply manufacturing high purity glycyrrhizic acid or D-galacturonic acid glycyrrhizic acid and the yield is high. The manufacturing method is characterized in that the 3rd hydroxyl group of glycyrrhetinic acid is subjected to glycosylation; then the 2' position is subjected to selective galactosylation or glycosylation, and after de-protection, selective oxidation of primary hydroxyl group is performed.

Description

technical field [0001] The present invention relates to a method for producing glycyrrhizic acid and galacturoglycyrrhizic acid (English: galacturoglycyrrhizic acid, Japanese: galacturoglycyrrhizic acid) chemically synthesized and an intermediate used in the production method. Background technique [0002] Glycyrrhizae is a crude drug widely used in traditional Chinese medicines, sweeteners, etc., and glycyrrhizic acid, which is a main component thereof, is a compound that has therapeutic effects on liver damage and the like. Glycyrrhizic acid is defined in the Japanese Pharmacopoeia as a quantitative component of crude drug licorice and Chinese medicines containing licorice, and its content is regulated. In addition, commercially available glycyrrhizic acid (GLY) is used as a standard substance, and analysis by HPLC is stipulated as a quantitative method. In recent years, due to the development of analysis technology, it has been found that in the HPLC chromatogram, the pea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/256C07H1/00C07J63/00
CPCC07H1/00C07H15/256C07J63/008
Inventor 小关雄太
Owner TSUMURA
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