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Rhodiola sacra glycoside derivative and its preparation method and use

A technology of salidroside and derivatives, applied in the field of medicine, can solve the problems of cumbersome reaction operation, low total yield and high cost, and achieve the effects of simplifying the process, reducing pollution and improving the yield

Inactive Publication Date: 2006-01-11
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The defect of this synthetic method is that the reaction operation is loaded down with trivial details, and the solvent that adopts the big toxicity such as benzene is easy to pollute the environment; Adopt expensive reagents such as Pd-C lithium aluminum hydride to make cost higher; And yield is low, and total yield is all lower than 50 %, [Li Guoqing, Li Zhan

Method used

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  • Rhodiola sacra glycoside derivative and its preparation method and use
  • Rhodiola sacra glycoside derivative and its preparation method and use
  • Rhodiola sacra glycoside derivative and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Preparation of 1-(4-hydroxy)phenethyl-β-D-glucopyranoside (salidroside, Compound No. 1).

[0042] Nitrogen was passed into a 50ml round bottom flask for protection, 30ml of anhydrous dichloromethane, 1g (7.5mmol) of 4-hydroxyphenethyl alcohol, 1.65g (6mmol) of silver carbonate were added, and the reaction was carried out at room temperature for 30 minutes in the dark under stirring . Add 2.65 g (6.5 mmol) of 2,3,4,6-tetra-O-acetyl-α-D-bromoglucopyranose and 0.83 g (3 mmol) of silver carbonate, and react at room temperature for 24 hours. After filtration, the solvent was distilled off under reduced pressure to obtain a viscous colorless residue, which is 1-(4-hydroxy)phenylethyl-β-D-glucopyranoside acetylated with sugar hydroxy groups.

[0043] Add 20ml (27mM) of methanol solution dissolved with sodium methoxide to the above residue, react at room temperature for 20 hours, concentrate under reduced pressure, separate with silica gel G column chromatography, a...

Embodiment 2

[0044] Example 2: Preparation of 1-(4-hydroxy)phenethyl-β-D-galactopyranoside (Compound No. 17).

[0045] Nitrogen was passed into a 50ml round bottom flask, 30ml of anhydrous dichloromethane, 1g (7.5mmol) of 4-hydroxyphenethyl alcohol, 1.65g (6mmol) of silver carbonate were added, and the reaction was carried out at room temperature in the dark for 30 minutes under stirring, and then added 2.65 g (6.5 mmol) of 2,3,4,6-tetra-O-acetyl-α-D-bromogalactopyranose and 0.83 g (3 mmol) of silver carbonate were reacted at room temperature for 24 hours. After filtration, the solvent was distilled off under reduced pressure to obtain a viscous colorless liquid, which was 1-(4-hydroxy)phenethyl-β-D-galactopyranoside acetylated with sugar hydroxy groups.

[0046] Add 20ml (27mM) of methanol solution dissolved with sodium methoxide into the above solution, react at room temperature for 20 hours, concentrate under reduced pressure, separate with silica gel G column chromatography, and use ch...

Embodiment 3

[0047] Example 3: Preparation of 1-(3-hydroxy)phenethyl-β-D-glucopyranoside (Compound No. 2).

[0048] Nitrogen was passed into a 50ml round bottom flask, 30ml of anhydrous dichloromethane, 1g (7.5mmol) of 3-hydroxyphenethyl alcohol, 1.65g (6mmol) of silver carbonate were added, and the reaction was carried out at room temperature in the dark for 30 minutes under stirring, and then added 2,3,4,6-Tetra-O-acetyl-α-D-bromoglucopyranose 2.65g (6.5mmol), silver carbonate 0.83g (3mmol), react at room temperature for 24 hours, filter, evaporate under reduced pressure Solvent, a viscous colorless residue was obtained, which was sugar hydroxyacetylated 1-(3-hydroxy)phenethyl-β-D-glucopyranoside.

[0049] Add 20ml (27mM) of methanol solution dissolved with sodium methoxide to the above residue, react at room temperature for 20 hours, concentrate under reduced pressure, separate with silica gel G column chromatography, use chloroform and methanol (4:1) as developing solvent, and obtain t...

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Abstract

A salidroside derivative is disclosed, which can be used to prepare the antioxidizing medicines. Its preparing process is also disclosed, which features simple process, high output rate, low cost and less environmental pollution.

Description

technical field [0001] The invention relates to the technical field of medicine, and relates to salidroside series derivatives, a preparation method of salidroside and the derivatives thereof, and the use of the salidroside derivatives for preparing antioxidant drugs. Background technique [0002] Salidroside, English name salidroside, chemical name "p-hydroxyphenethyl-β-D-glucopyranoside (p-hydroxyphenethyl-β-D-glucoside)", systematic name: 1-(4-hydroxy)benzene Ethyl-β-D-glucopyranoside is an active compound extracted from medicinal plants, mainly from the plateau medicinal plant "Rhodiola sachalinensis" and the commonly used traditional Chinese medicine "Ligustrum lucidum" ( Ligustrum lucidum) extracted from. [Xu Baojun, Zheng Yinan, Li Xianggao. New progress in the research of Rhodiola plants. Chinese Medicinal Materials, 2000, 23(9); Shi Lifu, Cai Qin, Cao Yingying, et al. Chemical constituents and pharmacological effects of the traditional Chinese medicine Ligustrum...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/18A61K31/7028A61P39/06
Inventor 石力夫蔡溱姚斌
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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