Method for asymmetrically synthesizing glabridin with optical purity

A technology of optical purity and glabridin, which is applied in organic chemistry methods, organic chemistry, bulk chemical production, etc., can solve the problems of human toxicity and expensive raw materials, and achieve convenient operation, good product yield, and low cost Effect

Inactive Publication Date: 2020-07-03
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the raw materials of this method are expensive, and some raw materials such as p-cymene are toxic to the human body and easily cause accidents such as combustion and explosion.

Method used

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  • Method for asymmetrically synthesizing glabridin with optical purity
  • Method for asymmetrically synthesizing glabridin with optical purity
  • Method for asymmetrically synthesizing glabridin with optical purity

Examples

Experimental program
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Effect test

Embodiment 1

[0047] (1) Synthesis of 7-benzyloxy chroman-4-one (compound 2)

[0048] In a three-neck flask equipped with a thermometer and a condenser, accurately weigh the KOH solid (0.11 mol) and 95% ethanol (40 mL), heat it to full dissolution, and add 7-hydroxychroman-4-one (0.1 mol), The obtained solution was slowly added dropwise to the refluxing benzyl chloride (0.125mol) ethanol solution (20ml), the dropping time was about 1h, after the dropping was completed, the reaction was continued for 1h at the reflux temperature. After the reaction, the solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol to obtain compound 2 with a yield of 87%.

[0049] 2) Synthesis of 7-benzyloxy-2H-chroman-4-yl acetate (compound 3)

[0050] Put compound 2 (1mmol), propylene acetate (3mmol) and p-toluenesulfonic acid (0.1mmol) in a reaction flask, stir and heat to reflux for 24h, cool to room temperature, distill the solvent under reduced pressure, and dissolve the o...

Embodiment 2

[0062] The synthesis of compounds 3, 4, 5, 6, 7 and R-glycyrrhizin is the same as that of Example 1, except for the synthesis of compound 2.

[0063] Synthesis of compound 2:

[0064] In a three-necked flask equipped with a thermometer and a condenser, accurately weigh out 0.11 mol of NaOH solid and 40 mL of 95% ethanol, heat them to full dissolution, add 7-hydroxychroman-4-one, and slowly drop the resulting solution Add to the 0.125mol benzyl chloride ethanol solution (20ml) that has refluxed, and the dripping time is about 1h. After the dripping is completed, the reaction is continued for 1h at the reflux temperature. After the reaction, the solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol to obtain compound 2 with a yield of 85%.

Embodiment 3

[0066] The synthesis of compounds 3, 4, 5, 6, 7 and R-glycyrrhizin is the same as that of Example 1, except for the synthesis of compound 2.

[0067] Synthesis of compound 2:

[0068] Compound 1 (0.1 mol) and potassium carbonate (0.12 mol) were added to 100 mL of acetone at room temperature, and then benzyl bromide (0.12 mol) was slowly added, and the reaction was carried out overnight. After the reaction, it was filtered, the solvent was evaporated under reduced pressure, and recrystallized with ethanol to obtain compound 2 with a yield of 88%.

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Abstract

The invention discloses a method for asymmetrically synthesizing glabridin with optical purity, belonging to the field of organic synthesis. According to the invention, 7-hydroxychroman-4-one is usedas a raw material and is subjected to seven successive reactions including a protecting group protection reaction, an enol esterification reaction, an asymmetric addition reaction, a carbonyl reduction reaction, a phenolic hydroxyl protecting group removal reaction, a cyclization reaction and a demethylation reaction so as to finally prepare glabridin with optical purity. The optically pure glabridin is obtained by asymmetrically introducing a chiral center by using a palladium catalyst and an organophosphorus ligand; reaction conditions are mild; operation is convenient; and the method is suitable for industrial application. The raw material is easy to obtain and low in cost, and the product is good in yield and high in stereoselectivity.

Description

Technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for asymmetrically synthesizing optical purity glycyrrhizin. Background technique [0002] Glycyrrhiza glabra (Glycyrrhiza glabra) is a perennial herb that grows in southern Europe, Asia, and the Mediterranean. It is widely planted in Russia, Spain, Iran and India, as well as in Xinjiang, China. [0003] Glabridin is one of the main flavonoids in Glycyrrhiza glabra. Glycyrrhizin shows a strong anti-free radical oxidation effect in the cytochrome P450 / NADPH oxidation system, which can obviously inhibit the free radicals generated in the metabolism process in the body, so as to avoid oxidation-sensitive biological macromolecules (low density lipoprotein LDL DNA) and cell walls are oxidatively damaged by free radicals, which can prevent certain pathological changes related to free radical oxidation, such as atherosclerosis and cell senescence. Therefore, Glycyrrhizin n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCC07D493/04C07B2200/07Y02P20/55
Inventor 蒋德旗臧青民章烨雯李海东
Owner YULIN NORMAL UNIVERSITY
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