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A kind of chemical synthesis method of forsythin

A technology for chemical synthesis and forsythin, applied in chemical instruments and methods, organic chemistry, pharmaceutical formulations, etc., can solve problems such as unfavorable operation, hydrobromic acid corrosion, low synthesis yield, etc. Easy-to-source effects

Active Publication Date: 2019-03-12
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

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  • A kind of chemical synthesis method of forsythin
  • A kind of chemical synthesis method of forsythin
  • A kind of chemical synthesis method of forsythin

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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 invention relates to a method for chemically synthesizing forsythin. In the method of the invention, the glycosyl acceptor forsythin and the glycosyl donor are dissolved in an organic solvent and then subjected to glycosidation reaction to obtain tetraacyl forsythin; and then Dissolving tetraacyl forsythin in an organic solvent, then adding sodium methoxide to carry out deacylation reaction, then adding an acidic pH regulator to adjust the pH value of the reaction mixture to neutral, and finally undergoing purification treatment to obtain the product. 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.

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 dry fruit of Forsythia suspensa (Thunb.) Vahl in the family Oleaceae (Oleaceae), mainly distributed in Henan, Shanxi, Shaanxi, Shandong and other places in my country. In addition, Hubei, Hebei, It is also distributed in Sichuan and Gansu. 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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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/04C07H1/00A61K31/7048A61P31/14A61P31/16A61P31/22
CPCC07H1/00C07H15/26A61P31/14A61P31/16A61P31/22A61K31/7048C07H17/04
Inventor 樊宏宇富力
Owner 富力