Efficient total synthesis method and application of natural product schaftoside

A natural product, the technology of schafposide, used in the fields of chemistry and medicine

Active Publication Date: 2021-07-30
ZHENGZHOU YUHEYUAN BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far there is no report on the chemical syn...

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  • Efficient total synthesis method and application of natural product schaftoside
  • Efficient total synthesis method and application of natural product schaftoside
  • Efficient total synthesis method and application of natural product schaftoside

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preparation example Construction

[0043] Such as figure 1 As shown, the efficient total synthesis method of the natural product schaftoside provided by the examples of the present invention comprises the following steps:

[0044] S101, naringenin is selectively protected by tert-butyldimethylsilyl chloride TBSCl and acetyl chloride in an organic solvent to obtain intermediate compound 2; intermediate compound 2 is hydroborated in a solvent A deoxygenation reaction occurs under the action of sodium to obtain intermediate compound 3;

[0045] S102, the intermediate compound 3 undergoes an O-C rearrangement reaction with the acetyl-protected glucose trichloroacetimide ester donor under the action of a catalyst to obtain the intermediate compound 5; the silicon group is removed under acidic conditions or an environment containing a fluorine reagent The protecting group gives intermediate compound 6;

[0046] S103, the intermediate compound 6 and the acetyl-protected L-arabinose trichloroacetimide ester donor und...

Embodiment 1

[0051] The purpose of the present invention is to carry out high-efficiency total synthesis of schafutasides and obtain sufficient amount to expand the application of biological activity.

[0052] Related analysis shows that the synthesis of similar flavonoid carbon glycosides is cumbersome and cannot be produced on a large scale. We have established a new method for the synthesis of schafutasides, which has been efficiently synthesized and can be prepared on a large scale. The technical solution of the present invention is, the synthetic method of flavonoid carboglycoside compound schaftoside, and its compound structure is as follows:

[0053]

[0054] The method includes the following steps:

[0055]

[0056] (1) Naringenin was selectively protected by tert-butyldimethylsilyl chloride (TBSCl) and acetyl chloride in an organic solvent to obtain intermediate compound 2. In the reaction, the protecting group at the C7 position of naringenin can be selected from tert-but...

Embodiment 2

[0067] (1) Synthesis of intermediate compound 2:

[0068] Naringenin (5.00g, 18.37mmol), Et 3 N (3.06mL, 22.04mmol) was dissolved in THF (50mL) to lower the reaction temperature to 0°C, then TBSCl (3.32g, 22.04mmol) was dissolved in THF (10mL), and slowly added dropwise to the reaction solution. After 2 hours of reaction at room temperature, TLC (Petroleum–EtOAc, 1:1) monitored the reaction of the raw materials. After the reaction was completed, the temperature of the reaction solution was lowered to 0°C, and Et 3 N (7.66mL, 55.11mmol), then AcCl (3.27mL) dissolved in 20mL THF solution was slowly added dropwise into the solution, paying attention to controlling the internal temperature, and quenching the reaction with saturated aqueous sodium bicarbonate solution after 2h. Dichloromethane ( 3×30 mL) was extracted from the reaction solution, dried over anhydrous sodium sulfate, filtered, and the residue concentrated under reduced pressure was separated by column chromatography...

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Abstract

The invention belongs to the technical field of chemistry and medicine, and discloses an efficient total synthesis method and application of a natural product schaftoside. The method comprises the steps of subjecting naringenin, tert-butyldimethylsilyl chloride and acetyl chloride to reaction to obtain an intermediate compound 2, and conducting deoxidation reaction to obtain an intermediate compound 3; carrying out rearrangement reaction on the intermediate compound 3 to obtain an intermediate compound 5, and removing a silicon-based protecting group to obtain an intermediate compound 6; carrying out rearrangement reaction on the intermediate compound 6 to obtain an intermediate compound 8; reacting the intermediate compound 8 with benzyl bromide in potassium carbonate to obtain an intermediate compound 9; oxidizing the intermediate compound 9 by ceric ammonium nitrate and pyridinium dichromate to obtain an intermediate compound 10; removing benzyl from the intermediate compound 10 to obtain an intermediate compound 11; and catalyzing the intermediate compound 11 to obtain an intermediate compound 12, and removing acetyl to obtain a target product compound. The method is mild in reaction condition, convenient to operate, economical in raw materials and capable of being used for industrial preparation.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and in particular relates to a high-efficiency total synthesis method and application of a natural product schaftoside. Background technique [0002] At present, flavone glycosides are compounds formed by linking flavone mother nuclei with glycoside ligands. Those linked to phenolic hydroxyl groups with carbon-oxygen bonds are called flavone oxyglycosides, and those linked to aryl carbons with carbon-carbon bonds are called flavone carbon glycosides. It has a wide range of physiological activities such as anti-inflammation, anti-infection, anti-cancer, neuroprotection, wound regeneration, hypoglycemic and antihypertensive / vasodilation activities. The activity of flavone glycoside-linked glycosyl ligands is quite different from that of flavone aglycones. Since sugar chains are involved in almost all life processes such as cell differentiation, development, immunity, aging, carcinoge...

Claims

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Application Information

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IPC IPC(8): C07D407/14A61P31/14A61P3/10A61P9/12A61P1/16A61P29/00A61P39/06
CPCC07D407/14A61P31/14A61P3/10A61P9/12A61P1/16A61P29/00A61P39/06Y02P20/55
Inventor 刘军杜宇国尚呈翔赵传芳
Owner ZHENGZHOU YUHEYUAN BIOTECHNOLOGY CO LTD
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