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Method for catalytic synthesis of salidroside

A salidroside and synthetic method technology, applied in chemical instruments and methods, organic chemistry, bulk chemical production, etc., can solve the problems of low yield and high production cost, and achieve high product yield, low cost, and catalytic The effect of improving efficiency

Active Publication Date: 2015-05-06
WUHAN SYNCHALLENGE UNIPHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In addition, Chinese patent CN201110184190.3 reported that Lewis acid (ZnCl 2 , AlCl 3 , SnCl 4 etc.) as a catalyst to react with pentaacetyl-β-D-glucopyranose, the product generated obtains the target product through deprotection, but the yield is low and the production cost is high. The reaction scheme is as follows:

Method used

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  • Method for catalytic synthesis of salidroside
  • Method for catalytic synthesis of salidroside
  • Method for catalytic synthesis of salidroside

Examples

Experimental program
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Effect test

Embodiment 1

[0044] (1) Synthesis of intermediate 4-benzyloxyphenethyl alcohol:

[0045] Dissolve 600g (4.348mol) of 4-hydroxyphenethyl alcohol in 1 liter of DMF. After dissolving, add 178g (4.45mol) of sodium hydroxide and stir for half an hour. Then add 481g (4.829mol) of benzyl chloride. TLC monitors that there is no raw material benzyl chloride. For post-treatment, it was directly poured into ice water, stirred for half an hour, filtered, washed with water, and dried to obtain 842 g of white solid, with a yield of 85%.

[0046] (2) Preparation of 2-(4-benzyloxyphenyl)ethyl-(2,3,4,6-O-tetra-acetyl)-β-D-glucopyranoside:

[0047] Add 273g (0.70mol) of peracetyl glucose, 191.5g (0.84mol) of 4-benzyloxy phenethyl alcohol, 29g (0.21mol) of zinc chloride and 13.6g (0.14mol) of magnesium chloride directly into 1.5L of chloroform Stir, react at 60°C for 10 hours and then desolvate to obtain off-white solid 2-(4-benzyloxyphenyl)ethyl-(2,3,4,6-O-tetra-acetyl)-β-D-pyran Glucoside 289g (0.51mol), the yi...

Embodiment 2

[0065] The preparation of 2-(4-benzyloxyphenyl) ethyl-(2,3,4,6-O-tetra-acetyl)-β-D-glucopyranoside: 200g (0.513 mol), 196g (0.86mol) of 4-benzyloxy phenethyl alcohol, 129g (0.97mol) of aluminum trichloride, 50g (0.513mol) of magnesium chloride, directly added to 1.2L of chloroform and stirred, reacted at 60℃ for 10h, and then dissolved , To obtain 200 g (0.36 mol) of off-white solid, with a yield of 70%.

Embodiment 3

[0067] Preparation of 2-(4-benzyloxyphenyl) ethyl-(2,3,4,6-O-tetra-acetyl)-β-D-glucopyranoside: 279 g (0.717 mol), 196g (0.86mol) of 4-benzyloxyphenethyl alcohol, 186g (0.717mol) of tin chloride and 44g (0.717mol) of magnesium fluoride are directly added to 1.6L of dichloroethane and stirred, and reacted at 60°C for 15h After desolvation, 281 g (0.49 mol) of off-white solid was obtained with a yield of 68%.

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Abstract

The invention discloses a method for catalytic synthesis of salidroside. The method comprises the following steps: enabling total acetyl glucose to react with 4-benzyloxy-phenethyl alcohol under the action of a catalyst to obtain 2-(4-benzyloxyphenyl)ethyl-(2,3,4,6-O-tetra-acetyl)-beta-D-glucopyranoside, wherein the catalyst is tin chloride, zinc oxide, aluminum trichloride, boron fluoride or copper chloride, or a mixture of one of tin chloride, zinc oxide, aluminum trichloride, boron fluoride and copper chloride as well as magnesium fluoride, magnesium chloride, magnesium bromide or magnesium iodide; and removing an acetyl protective group from the product in the presence of an organic base to obtain 2-(4-benzyloxyphenyl)ethyl-beta-D-glucopyranoside, and introducing hydrogen into 2-(4-benzyloxyphenyl)ethyl-beta-D-glucopyranoside under the catalysis of palladium and carbon to perform reduction reaction so as to remove a benzyl protective group, thereby obtaining 2-(4-hydroxyphenyl)ethyl-beta-D-glucopyranoside. The method disclosed by the invention has the outstanding characteristics that the yield is high, the total acetyl glucose is subjected to three steps of reaction, the total yield can reach 63%, the process is simple, the cost is low, and the method is suitable for industrial mass production.

Description

Technical field [0001] The invention relates to a method for the catalytic synthesis of natural product salidroside (Salidroside). Background technique [0002] The main component of Chinese herbal medicine Rhodiola is salidroside (Formula 1, CAS: 10338-51-9, 2-(4-hydroxyphenyl)ethyl-β-D-glucopyranoside), chemical name: 2-(4-hydroxybenzene) Group) ethyl-β-D-glucopyranoside. [0003] [0004] Salidroside has a wide range of physiological activities and has a regulatory effect on the cardiovascular system: it has a protective effect on myocardial cells after hypoxia and reoxygenation, which can maintain normal pulsation frequency of myocardial cells after hypoxia and reoxygenation, and reduce LDH release. Maintain the normal ultrastructure of myocardial cell membrane, myofibrils, and mitochondria. Effects on the central nervous system: Salidroside can enhance the excitability of the brainstem reticulum system, stimulate the spontaneous activity of the cortical sensory-motor area, t...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00
CPCC07H1/00C07H15/18Y02P20/55
Inventor 巨修练袁振昌刘慧王均震郑文钺汤兴国
Owner WUHAN SYNCHALLENGE UNIPHARM INC
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