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Salidroside chemical synthesis method for industrialization

A salidroside and compound technology, applied in chemical instruments and methods, organic chemistry, bulk chemical production, etc., can solve the problems that product separation must rely on column chromatography, process industrialization amplification, and complex reaction products, etc., to achieve good results Effects of crystallinity, reduction of contamination, and simplification of purification operations

Active Publication Date: 2012-01-04
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method uses cheap and easy-to-obtain β-pentaacetylglucose as a raw material, tyrosol does not need to be protected, and the reaction steps are the shortest in all salidroside chemical synthesis related documents, but also due to the alcoholic hydroxyl group of tyrosol and the phenolic All hydroxyl groups can undergo glycosylation reactions, so it will cause problems such as complex reaction products, low yields, and separation of products in each step must rely on column chromatography, which greatly reduces the possibility of industrial scale-up of this process

Method used

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  • Salidroside chemical synthesis method for industrialization
  • Salidroside chemical synthesis method for industrialization
  • Salidroside chemical synthesis method for industrialization

Examples

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Embodiment 1

[0043] Embodiment 1: the preparation of 2-(4-benzoyloxyphenyl) ethanol

[0044] Dissolve tyrosol (1kg, 7.24mol) in 10L ethyl acetate, add 1.2L (1.2eq) triethylamine, and stir in an ice bath; dissolve 1L (1.2eq) of benzoyl chloride in 2L ethyl acetate, add dropwise into the above solution. After dropping, react at room temperature for 1 h. The reaction solution was filtered, washed three times with a saturated aqueous solution of sodium carbonate and three times with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated. Petroleum ether: chloroform=5:1 recrystallized, filtered and dried. 1.23 kg of white scaly solid was obtained, with a yield of 70.1%. The melting point is 66.2-67.9°C.

[0045] 1 H NMR (400MHz, CDCl 3 )δ8.20(d, J=7.7Hz, 2H), 7.63(t, J=7.4Hz, 1H), 7.51(t, J=7.7Hz, 2H), 7.28(d, J=8.4Hz, 2H) , 7.16(d, J=8.4Hz, 2H), 3.86(t, J=6.5Hz, 2H), 2.88(t, J=6.6Hz, 2H), 1.65(br, 1H). 13 C NMR (100MHz, CDCl 3 )δ165.46, ...

Embodiment 2

[0046] Embodiment 2: the preparation of 2-(4-benzoyloxyphenyl) ethanol

[0047]Tyrosol (1kg, 7.24mol) was dissolved in 10L ethyl acetate, 1.2L (1.2eq) triethylamine was added, stirred under ice bath; benzoyl chloride 1L (1.2eq) was dissolved in 2L ethyl acetate, drop Add to the above solution. After dropping, react at room temperature for 1 h. The reaction solution was filtered, washed three times with a saturated aqueous solution of sodium carbonate and three times with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated. Recrystallized from isopropyl ether, filtered and dried. 1.3 kg of white scaly solid was obtained, with a yield of 74.1%. The melting point is 66.3-67.9°C.

Embodiment 3

[0048] Embodiment 3: the preparation of 2-(4-benzoyloxyphenyl) ethanol

[0049] Dissolve tyrosol (1kg, 7.24mol) in 10L ethyl acetate, add 1.2L (1.2eq) triethylamine, stir under ice bath; dissolve 1.04L (1.2eq) of benzoyl bromide in 2L ethyl acetate , added dropwise to the above solution. After dropping, react at room temperature for 1 h. The reaction solution was filtered, washed three times with a saturated aqueous solution of sodium carbonate and three times with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated. Recrystallized from isopropyl ether, filtered and dried. 1.25 kg of white scaly solid was obtained, with a yield of 71.3%. The melting point is 66.1-67.9°C.

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Abstract

The invention discloses a method for chemically synthesizing natural product salidroside. In the method, lewis acid serving as a catalyst, tyrosol of acyl protected phenolic hydroxyl serving as a glycosylation receptor, and beta-D-5 acetyl glucose serving as glycosylation donor perform a glycosylation reaction to obtain 1-[2-(4-acyloxy phenyl) ethyl]-2,3,4,6-O-tetraacetyl-beta-D-glucopyranoside; and acyl protecting group is removed in an alkaline condition to obtain salidroside. Compared with the traditional method, the method has easily available raw materials, the glycosylation receptor, the glycosylation product and the final product can be prepared through recrystallization, column chromatography and other purification processes are eliminated, the reaction step is short, the preparation process is simple, the glycosylation reaction catalyst has low cost and is easily available, so that the preparation cost is remarkably reduced; and a heavy metal salt catalyst is not used in the reaction, so that the synthesis product is more suitable to be used as a raw material of medicaments and health-care products. The method is suitable for industrial production of salidroside.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemicals, and more specifically relates to a chemical synthesis method of the natural product salidroside suitable for industrialization. Background technique [0002] Rhodiola is a perennial herbaceous plant belonging to the Sedum family Rhodiola. There are nearly 100 species of this genus in the world, and there are many varieties. It is a high-altitude, cold-resistant plant. Salidroside is one of the main active ingredients of Rhodiola rosea, a medicinal plant in Tibetan medicine in my country. Modern pharmacological research results show that salidroside has a protective effect on myocardial injury, has anti-hypoxia, anti-radiation, anti-fatigue, anti-aging, immune function regulation and detoxification effects, and has a two-way regulation effect on blood pressure and blood sugar. It has various effects such as sedation, anti-microwave radiation, promotion of protein metabolism, anti-infl...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00C07C69/78C07C67/14C07C205/57C07C201/12
CPCY02P20/55
Inventor 李中军李辉马庆李庆孟祥豹李树春
Owner PEKING UNIV
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