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Catalytic synthesis method of salidroside

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

Active Publication Date: 2017-09-19
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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  • Catalytic synthesis method of salidroside
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  • Catalytic synthesis method of salidroside

Examples

Experimental program
Comparison scheme
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, add 178g (4.45mol) of sodium hydroxide after dissolving, stir for half an hour, then add 481g (4.829mol) of benzyl chloride, TLC monitors that there is no raw material benzyl chloride Post-treatment, 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 peracetylglucose, 191.5g (0.84mol) of 4-benzyloxyphenethyl 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 remove the solvent to obtain off-white solid 2-(4-benzyloxyphenyl)ethyl-(2,3,4,6-O-tetra-acetyl)-β-D-pyran Glucoside 289g (0.51mol), yield 73...

Embodiment 2

[0065] 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-benzyloxyphenethyl alcohol, 129g (0.97mol) of aluminum trichloride, and 50g (0.513mol) of magnesium chloride were directly added to 1.2L of chloroform and stirred, reacted at 60°C for 10h, and precipitated , 200 g (0.36 mol) of an off-white solid was obtained, and the yield was 70%.

Embodiment 3

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

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Abstract

Disclosed is a method for catalytic synthesis of salidroside. The method comprises: 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)-β-D-glucopyranoside, the catalyst being tin chloride, zinc oxide, aluminum trichloride, boron fluoride or copper chloride, or a mixture formed by mixing one of tin chloride, zinc oxide, aluminum trichloride, boron fluoride and copper chloride with 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-β-D-glucopyranoside, and introducing hydrogen into 2-(4-benzyloxyphenyl)ethyl-β-D-glucopyranoside under the catalysis of palladium and carbon to perform a reduction reaction so as to remove a benzyl protective group, thereby obtaining 2-(4-hydroxyphenyl)ethyl-β-D-glucopyranoside. The present invention has the outstanding characteristics that the yield is high, the total acetyl glucose is subjected to three steps of reactions, the total yield can reach 63%, the process is simple, the cost is low, and the present invention is suitable for industrial mass production.

Description

technical field [0001] The invention relates to a catalytic synthesis method of a natural product salidroside. Background technique [0002] The main component of the Chinese herbal medicine Rhodiola is salidroside (Formula 1, CAS: 10338-51-9, 2-(4-hydroxyphenyl)ethyl-β-D-glucopyranoside), chemical name: 2-(4-hydroxybenzene base) 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 cardiomyocytes damaged by oxygen after hypoxia, can maintain the normal beating frequency of cardiomyocytes after hypoxia, and reduces the release of LDH. Maintain the normal ultrastructure of myocardial cell membranes, myofibrils, and mitochondria. Effects on the central nervous system: salidroside can enhance the excitability of the brainstem reticular system, stimulate the spontaneous potential activity of the cortical sensory-motor area, visual area and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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