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Chemical synthesis method of phillyrin

A technology for chemical synthesis and forsythin, applied in chemical instruments and methods, organic chemistry, pharmaceutical formulations, etc., can solve the problems of hydrobromic acid corrosiveness, unfavorable operation, low synthesis yield, etc., and achieve convenient source of raw materials and easy preparation The effect of cost reduction

Active Publication Date: 2016-04-06
富力
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The chemical synthesis of forsythin has been studied. In 2014, Fan Hongyu et al. used tetraacetyl-D-glucose-1-bromosugar and forsythin to carry out glycosylation reaction under the catalysis of phase transfer catalyst and base, and then used Deprotection of sodium methoxide to generate forsythin [Fan Hongyu, Fuli, Synthesis and structural characterization of forsythin, Liaoning Chemical Industry, 2014, 43, 241-243], but the synthesis yield of this method is low and tetraacetyl-D-glucose -1-Bromosugar needs bromination of pentaacetyl-β-D-glucose and 33% hydrobromic acid in acetic acid solution, and hydrobromic acid is corrosive, which is not conducive to operation

Method used

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  • Chemical synthesis method of phillyrin
  • Chemical synthesis method of phillyrin
  • Chemical synthesis method of phillyrin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1) Glycosidation reaction

[0043] Put forsythiatin (372mg, 0.001mol), 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl trichloroacetimidate (738mg, 0.0015mol) in a 100mL three-necked flask , wherein the molar ratio of forsythiatin to 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl trichloroacetimidate was 1:1.5, adding 20 mL of anhydrous dichloromethane , type aluminosilicate molecular sieve (744mg); then pass into inert gas nitrogen to carry out inert gas protection, stir for 0.5h, after mixing uniformly, add Lewis acid catalyst trimethylsilyl trifluoromethanesulfonate (TMSOTf, 0.06mL, 0.312 mmol), the molar ratio of Lewis acid catalyst to 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl trichloroacetimide ester is 1:5, the mass of molecular sieve and forsythiatin The ratio is 2:1, stirring at 0°C for glycosylation reaction for 10 hours;

[0044] After the Lewis acid deprives the hydrogen of the hydroxyl group of the reaction substrate forsythiatin, the generated active intermediate will b...

Embodiment 2

[0058] 1) Glycosidation reaction

[0059] Put forsythiatin (372mg, 0.001mol), 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (1.11g, 0.0015mol) in 100mL In a three-necked flask, where the molar ratio of forsythiatin and 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate is 1:1.5, add 20 mL of anhydrous dichloromethane, Type aluminosilicate molecular sieve (744mg), then pass into inert gas argon to carry out inert gas protection, after stirring for 0.5h, dropwise add Lewis acid catalyst silver trifluoromethanesulfonate 80mg (0.312mmol), Lewis acid catalyst and 2,3 , The molar ratio of 4,6-tetra-O-acetyl-D-glucopyranosyl trichloroacetimidate is 1:5, the mass ratio of molecular sieve to forsythiatin is 2:1, at 10℃ Stirring, carry out glycosylation reaction 8 hours;

[0060] Molecular sieves are added to remove the water generated by the reaction to ensure that the reaction proceeds in the positive direction.

[0061] 2) Quenching treatment

[0062]...

Embodiment 3

[0068] 1) Glycosidation reaction

[0069] Put forsythiatin (372mg, 0.001mol), 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl trichloroacetimidate (1.23g, 0.0025mol) in 100mL three ports In the flask, the molar ratio of forsythiatin and 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl trichloroacetimidate is 1:2.5, add 20 mL of anhydrous trichloro methane, Type aluminosilicate molecular sieve (744mg), then pass into inert gas nitrogen for inert gas protection, after stirring for 0.5h, add Lewis acid catalyst trimethylsilyl trifluoromethanesulfonate (0.08mL, 0.416mmol) dropwise, Lewis acid The molar ratio of catalyst to 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl trichloroacetimidate is 1:6, and the mass ratio of molecular sieve to forsythiatin is 2:1 , stirred at 0°C, and carried out glycosylation reaction for 10 hours;

[0070] 2) Quenching treatment

[0071] Add quencher triethylamine (0.416mmol) to the reaction mixture to quench the glycosylation reaction, the molar ratio of quencher triet...

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Abstract

The present invention relates to a method for chemical synthesis of phillyrin. According to the method, a glycosyl acceptor phillygenin and a glycosyl donor are dissolved in an organic solvent, a glycosylation reaction is performed to prepare tetra acyl phillyrin, the tetra acyl phillyrin is dissolved in an organic solvent, sodium methylate is added, a deacylation reaction is performed, an acidic pH value adjusting agent is added to adjust the pH value of the reaction mixture to achieve a neutral state, and finally a purification treatment is performed to obtain the product. According to the present invention, the advanced and practical characteristics of the production method comprise convenient raw material source, cheap and easily-available catalyst for the glycosylation reaction, significantly-reduced preparation cost, and industrial production achieving.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular, the invention relates to a method for chemically synthesizing forsythin. [0002] The advancement and practical value of the preparation method of the present invention lie in that the source of raw materials is convenient, the catalyst for the glycosylation reaction is cheap and easy to obtain, the preparation cost is obviously reduced, and it can be produced industrially. Background technique [0003] Forsythia is the dried fruit of Forsythia (Forsythia) plant Forsythia (Forsythia) in Oleaceae (Oleaceae), mainly distributed in Henan, Shanxi, Shaanxi, Shandong and other places in my country. In addition, Hubei, Hebei, Sichuan , Gansu is also distributed. It is often used to treat acute wind-heat cold, carbuncle sore, lymph node tuberculosis, urinary tract infection and other diseases. The main component of forsythia is forsythin (phillyrin), which has antiviral, antibacterial, ...

Claims

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Application Information

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IPC IPC(8): C07H17/04C07H1/00A61K31/7048A61P31/14A61P31/16A61P31/22
CPCA61P31/14A61P31/16A61P31/22C07H1/00C07H15/26A61K31/7048C07H17/04
Inventor 樊宏宇富力
Owner 富力
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