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Method of chemical synthesizing hongjingtian glycoside

A salidroside and chemical synthesis technology, applied in organic chemistry, sugar derivatives, etc., can solve the problems of multiple processes, high cost, and high price, and achieve the effect of shortening the reaction steps and reducing the production cost

Inactive Publication Date: 2007-02-14
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Tetraacetyl-D-glucose-1-bromosugar in the above method needs to be obtained by bromination of pentaacetyl-β-D-glucose and hydrobromic acid, and expensive precious metal salt silver carbonate is used as a glycosidation catalyst , In addition to the protection of the protective group on the sugar, the glycosidation product also needs to use palladium catalytic hydrogenation to remove the protective group on the phenolic hydroxyl group, so there are many procedures and the cost of industrialization is relatively high

Method used

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  • Method of chemical synthesizing hongjingtian glycoside

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 2 g of 4A molecular sieves to a solution of pentaacetyl-β-D-glucose (2.93 g, 7.5 mmol) in dichloromethane (30 ml), and stir for 1 hour under nitrogen protection. Then, tin tetrachloride (0.585ml, 5.0mmol) was added, immediately after the addition, a suspension of p-hydroxyphenethyl alcohol (0.69g, 5mmol) in dichloromethane (20ml) was added, and the reaction was stirred at room temperature for 2 hours. After the reaction was completed and allowed to stand, pour out the organic layer, then add ethyl acetate to the solid and stir for several minutes, pour out the organic layer, and repeat again. After the organic phases were combined, they were poured into saturated sodium bicarbonate (75ml) under stirring, and after the organic layer was separated, the aqueous layer was extracted with dichloromethane (3 × 15ml), and the organic layers were combined and washed with water (2 × 30ml). Then it was filtered on celite, and the solvent was distilled off under reduced pressur...

Embodiment 2

[0026] Add 2 g of 4A molecular sieves to a solution of pentaacetyl β-D-glucose (2.96 g, 7.5 mmol) in dichloromethane (30 ml), and stir for 1 hour under nitrogen protection. Then, boron trifluoride ether solution (0.63ml, 5.0mmol) was added, and immediately after the addition, a suspension of p-hydroxyphenylethanol (0.69g, 5mmol) in dichloromethane (20ml) was added, and the reaction was stirred at room temperature for 5 hours. 0.30 g of tetraacetyl salidroside was obtained.

[0027] The above-mentioned tetraacetyl salidroside was dissolved in anhydrous methanol (12.5 ml) containing sodium methoxide (0.07 g, 1.3 mmol), and stirred at room temperature for 12 hours. After the reaction was finished, an acidic resin was added to neutralize, and then the resin was filtered off. The filtrate was concentrated under reduced pressure, and separated and purified with a silica gel column to obtain 0.17 g of salidroside, with a total yield of 11%.

Embodiment 3

[0029] Add 2 g of 4A molecular sieves to a solution of pentaacetyl β-D-glucose (3.90 g, 1.0 mmol) in dichloromethane (30 ml), and stir for 1 hour under nitrogen protection. Then, tin tetrachloride (0.88ml, 7.5mmol) was added, immediately after the addition, a suspension of p-hydroxyphenethyl alcohol (0.69g, 5mmol) in dichloromethane (20ml) was added, and the reaction was stirred at room temperature for 2 hours. 0.56 g of tetraacetyl salidroside was obtained.

[0030] The above tetraacetyl salidroside was dissolved in anhydrous methanol (12.5 ml) containing sodium methoxide (0.14 g, 2.5 mmol), and stirred at room temperature for 24 hours. After the reaction was completed, an acidic resin was added for neutralization, and then the resin was filtered off. The filtrate was concentrated under reduced pressure and separated and purified with a silica gel column to obtain 0.33 g of salidroside, with a total yield of 22%.

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Abstract

The chemical process of synthesizing rhodiola glycoside includes the following steps: the Lewis acid catalyzed glycosidation between pentacetyl-beta-D-glucose and p-hydroxy phenethyl alcohol inside organic solvent to produce tetracetyl rhodiola glycoside; and the subsequent deacetylation of tetracetyl rhodiola glycoside inside the methanol solution of NaOCH3 to obtain rhodiola glycoside. Compared with traditional synthesis process, the present invention has the advantages of wide material source, less reaction steps and low preparation cost. The process of the present invention is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of pharmaceutical chemical industry, in particular to a method for chemically synthesizing salidroside. Background technique [0002] Rhodiola belongs to the sedum family. There are nearly a hundred species in the world, mostly distributed in the alpine regions of the northern hemisphere, and most of them grow at an altitude of 3500-5000 meters. In the place where Rhodiola is produced, people use it as a tonic and strong medicine, and it is also used to eliminate fatigue and resist cold; it has anti-aging, anti-fatigue, anti-hypoxia, anti-adverse stimulation, two-way regulation of the body, and inhibition of blood sugar rise. In 1976, the Soviet Union used rhodiola as an "adaptogen" drug, which was widely used in anti-fatigue, anti-aging, and improving mental and physical functions. In my country, Rhodiola rosea plants have been used to successfully develop injection preparations, oral liquid preparations and a varie...

Claims

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Application Information

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IPC IPC(8): C07H15/18
Inventor 吴金龙廖宇刘珊林
Owner ZHEJIANG UNIV
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