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New synthesis method of natural product Salvianolic Acid F

A natural product and new synthesis technology, applied in chemical instruments and methods, compounds of elements of group 4/14 of the periodic table, compounds of elements of group 5/15 of the periodic table, etc., can solve the problem of low yield and difficult source of raw materials To achieve the effect of high yield, unique and novel design, and less side reactions

Active Publication Date: 2017-10-20
王晓季 +1
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Problems solved by technology

[0005] The purpose of the present invention is to overcome the existing synthesis method existing raw material source is difficult to get, the problem such as low yield, aims to provide a new synthetic method of natural product Salvianolic Acid F

Method used

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  • New synthesis method of natural product Salvianolic Acid F
  • New synthesis method of natural product Salvianolic Acid F
  • New synthesis method of natural product Salvianolic Acid F

Examples

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Embodiment 1

[0027] 1) Using 4-methylcatechol, a compound of formula 8 as a raw material, first protected by a hydroxyl group, followed by a methyl radical reaction and then reacted with triphenylphosphine to obtain a phosphonium salt of formula 7:

[0028]

[0029] At 0°C, 4-methylcatechol (5.0g, 40.28mmol) was dissolved in N,N-dimethylformamide (DMF), and under nitrogen protection, imidazole (13.7g, 201.39mmol) and Tert-butyldimethylchlorosilane (TBSCl) (18.2 g, 120.83 mmol) was then raised to normal temperature and stirred overnight. Point the plate to monitor the reaction until it is complete. After that, the reaction was quenched with ice water, and then extracted with dichloromethane (3×150 mL). The organic phases were combined, washed with saturated NaCl solution, dried with anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. After the solvent was removed, 14.20 g of the compound of formula 9 was obtained by separation through a chromatographic column, with a yie...

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Abstract

The invention discloses a new synthesis method of a natural product Salvianolic Acid F. The method comprises the following steps: carrying out hydroxyl group protection on 4-methycatechol used as a raw material, carrying out a methyl radical reaction, and reacting the obtained methyl radical reaction product with triphenyl phosphine to obtain a phosphorus onium salt of formula 7; carrying out hydroxyl group protection, bromination and hydroxyl group deprotection on o-vanillin used as a raw material, carrying out methyl group deprotection on the hydroxyl group, and carrying out hydroxyl group protection to obtain a compound of formula 5; carrying out a Wittig reaction on the compound of formula 5 and the phosphorus onium salt of formula 7, carrying out lithium-halogen exchange under the action of n-butyllithium, and reacting the obtained exchange product with N,N-dimethyl formamide to obtain a compound of formula 3; carrying out an HWE reaction on the compound of formula 3 and phosphate ester of formula 4 to obtain a compound of formula 2; and carrying out hydroxyl deprotection and methyl ester hydrolysis to obtain the Salvianolic Acid F. The synthesis method has the advantages of novel and reasonable route, cheap and easily available raw materials, simple operating technology, mild reaction conditions, few side reactions, high yield and good repeatability.

Description

Technical field [0001] The present invention relates to a synthetic method of natural product intermediates, in particular to a new synthetic method of natural product SalvianolicAcid F. Background technique [0002] In the 1980s, Chen Zhengxiong et al. used various chromatographic techniques to separate more than a dozen salvianolic acids from the water-soluble components of Salvianolic Acid, including Salvianolic Acid F, during the systematic study of the water-soluble components of Salvia miltiorrhiza in the 1980s. The pharmacological activity shows that Salvianolic Acid F has significant anti-oxidation, anti-thrombosis, anti-liver fibrosis and prevention and treatment of diabetes and complications. Its good pharmacological and biological activities have attracted great interest from synthetic chemists, biologists and pharmacologists. The chemical structure of Salvianolic Acid F is as follows: [0003] [0004] Most salvianolic acid compounds are formed by combining Danshensu ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C59/48
CPCC07C51/09C07F7/1804C07F7/188C07F7/1892C07F9/5456C07C59/48
Inventor 王猛王奕锟武常委王子端李晓彤王博彭莹刘丽霞
Owner 王晓季
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