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3-hydroxy olefine acid derivative and its preparation and application

A technology for hydroxyalkenoic acid and derivatives, which is applied in the field of 3-hydroxyalkenic acid derivatives and its preparation and application, which can solve the problems of low efficiency, unfavorable preparation, inconvenient preparation of intermediates, etc., to ensure optical purity and enrich compounds Kind of effect

Inactive Publication Date: 2009-05-27
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the first method has higher requirement (lowfunctional group tolerance) to substrate, narrow scope of application, and is inconvenient to prepare intermediate, so every synthetic a kind of (R)- or (S)-3-hydroxyacid must be obtained from Starting from the "source" is low in efficiency and is not conducive to the preparation of compound libraries; and affected by factors such as substrate substituents, the second and third methods cannot ensure that the obtained products are optically pure (R)- or (S) -3-hydroxy acid; and, none of these three methods can effectively play a role in introducing functional groups such as carbonyl

Method used

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  • 3-hydroxy olefine acid derivative and its preparation and application
  • 3-hydroxy olefine acid derivative and its preparation and application
  • 3-hydroxy olefine acid derivative and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1, the synthesis of (S)-3-hydroxyl-4-pentenoic acid benzyl ester

[0053]

[0054] Add triethylamine (2.11 mL, 1.5 equiv.) to a solution of crude (S)-3-hydroxy-4-pentenoic acid (1.16 g, 10 mmol) in acetone (15 mL), cool to 0°C, and slowly drop Add benzyl bromide (1.45 mL, 1.2 equiv.), react at room temperature for 12 hours, concentrate and purify by column chromatography (silica gel column, petroleum ether: ethyl acetate volume ratio is 7:1-5:1 as mobile phase) (purchased from silica gel From Qingdao Ocean Chemical Co., Ltd., petroleum ether (60-90° C.) and ethyl acetate were purchased from Beijing Chemical Reagent Company) to obtain 1.70 g of oil, with a yield of 82.4%.

[0055] [ α ] D 15 = - 2.06 ( c 2.92 , CH 2 Cl...

Embodiment 2

[0058] Embodiment 2, the synthesis of (S)-3-O-acetyl-4-pentenoic acid benzyl ester

[0059]

[0060] A mixture of (S)-benzyl 3-hydroxy-4-pentenoate (206 mg, 1.0 mmol), pyridine (0.242 ml, 3 equiv.) and acetic anhydride (0.142 ml, 1.5 equiv) was stirred at room temperature Overnight, diluted with ethyl acetate, washed with water three times, dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography (silica gel column, petroleum ether: ethyl acetate volume ratio of 50:1 as mobile phase) (silica gel was purchased from Qingdao Haiyang Chemical Co., Ltd., petroleum ether (60-90° C.) and ethyl acetate were purchased from Beijing Chemical Reagent Company), and 240.2 mg of the product were obtained with a yield of 96%.

[0061] [ α ] D 15 = - 1.04 ( c = 1.43 , ...

Embodiment 3

[0064] Embodiment 3, the synthesis of (S)-3-O-tert-butyldimethylsilyl-4-pentenoic acid benzyl ester

[0065]

[0066] Dissolve (S)-3-hydroxy-4-pentenoic acid benzyl ester (154.5 mg, 0.75 mmol) and imidazole (128 mg, 1.88 mmol) in 2.5 ml of N, N-dimethylformamide, and add Add tert-butyldimethylsilyl chloride (147 mg, 0.97 mmol) in batches, add 20 ml of water after 6 hours, extract with ethyl acetate, concentrate the extract after drying over anhydrous sodium sulfate, and purify by column chromatography (silica gel column, The volume ratio of petroleum ether: ethyl acetate is 50:1 as the mobile phase) (silica gel was purchased from Qingdao Ocean Chemical Co., Ltd., petroleum ether (60-90 ° C) and ethyl acetate were purchased from Beijing Chemical Reagent Company), and 155 mg of the product was obtained. Yield 87.5%.

[0067] [ α ] D 27 = - 1.70 ...

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Abstract

The present invention discloses one kind of 3-hydroxy olefine acid derivative in the structure as shown and its preparation process and application. By means of the inherent chirality of the material and the cross-metathesis of olefine, the product of the present invention, 3-hydroxy olefine acid, has high optical purity. The present invention lays foundation for the industrial preparation of 3-hydroxy olefine acid derivative.

Description

technical field [0001] The invention relates to a 3-hydroxyalkenoic acid derivative and its preparation method and application. Background technique [0002] Olefin cross-metathesis reaction (Olefin Cross-metathesis) is an effective means to construct carbon-carbon bonds. In recent years, with the continuous development of various catalysts, the recycling and reuse of catalysts has become possible, not only the catalytic activity has been significantly improved, the reaction time has been gradually shortened, and the required reaction temperature has also been greatly reduced. Sensitivity has been reduced. [0003] The (R)- or (S)-3-hydroxy acid fragment is a common fragment in natural products such as glycolipids and cyclic peptides. It not only exists in all lipid A (Lipid A) molecules, but also participates in the construction of sulfobacin A , the molecular skeleton of natural products such as lobatamide C. According to comprehensive literature reports, there are thre...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/73C07F7/18
Inventor 俞初一乔岩
Owner INST OF CHEM CHINESE ACAD OF SCI
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