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Fully-synthesizing method for (2R,3S)-epoxy-9-(aprylene-1-OL

A total synthesis and octene technology, applied in organic chemistry and other fields, can solve problems such as difficult to obtain a large amount of clinical research, complex and cumbersome extraction process, etc., and achieve the effect of high yield and simple separation and purification operation

Inactive Publication Date: 2007-11-14
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Due to the low content of these active substances in plants, the extraction process is complex and cumbersome, and it is difficult to obtain a large amount and carry out subsequent animal experiments and clinical studies, so total synthesis has become an inevitable way, (2R, 3S)-epoxy-9- Octen-1-ol is a common intermediate in the synthesis of these natural products, and so far no report has been found on the total synthesis of this important intermediate

Method used

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  • Fully-synthesizing method for (2R,3S)-epoxy-9-(aprylene-1-OL
  • Fully-synthesizing method for (2R,3S)-epoxy-9-(aprylene-1-OL
  • Fully-synthesizing method for (2R,3S)-epoxy-9-(aprylene-1-OL

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1) In a 500ml three-necked flask with electric stirring, add 2.84g (50mmol) potassium borohydride (reducing agent), 0.264g (1mmol) 18-crown-6 (phase transfer catalyst), and 150ml tetrahydrofuran respectively under stirring, Cool to 5°C, slowly add 0.113ml (1mmol) TiCl dissolved in 10ml tetrahydrofuran dropwise 4 (titanium reagent, titanium tetrachloride), and then heated up to 30° C., and reacted for 0.5 hours to obtain a titanium composite (catalyst composite). Then 7.76ml (50mmol) of 1,7-octadiene (compound 2) was added to the above reaction system, and the reaction was continued for 4 hours to obtain an organoboron compound. Then the above reaction system was cooled to 5°C, 60ml of 6mol / L sodium methoxide and 120ml of hydrogen peroxide (hydrogen peroxide) (30% mass, concentration about 8.8mol / L) were added, then the temperature was raised to 65°C, reacted for 0.5 hours, and then used Diethyl ether was extracted 3 times, 50ml each time, and concentrated to obtain the...

Embodiment 2

[0038] 1) In a 500ml three-necked flask with electric stirring, add 1.9g (50mmol) sodium borohydride (reducing agent), 0.264g (1mmol) 18-crown-6 (transfer catalyst) and 150ml tetrahydrofuran under stirring respectively, Cool to 5°C, slowly add 0.113ml (1mmol) TiCl dissolved in 10ml tetrahydrofuran dropwise 3 (titanium reagent, titanium trichloride), and then heated up to 30° C., and reacted for 0.5 hours to obtain a titanium composite (catalyst composite). Then 7.76ml (50mmol) of 1,7-octadiene (compound 2) was added to the above reaction system, and the reaction was continued for 4 hours to obtain an organoboron compound. Then the above reaction system was cooled to 5°C, 60ml of 6mol / L sodium methoxide and 120ml of hydrogen peroxide (hydrogen peroxide) (30% mass, concentration about 8.8mol / L) were added, then the temperature was raised to 65°C, reacted for 0.5 hours, and then used Diethyl ether was extracted 3 times, 50ml each time, and concentrated to obtain the crude produc...

Embodiment 3

[0044] 1) with embodiment 1

[0045] 2) In a 250ml three-necked flask, place a constant pressure dropping funnel, an electric stirrer and a thermometer respectively, add 80ml of dry dichloromethane, protect it under argon at -70°C, first add oxalyl chloride (8.16ml, 90mmol), and then use a constant pressure Add DMSO (dimethyl sulfoxide) (13.92ml, 180mmol) into the dropping funnel, dilute with 20ml of dichloromethane, add dropwise to the flask, the rate of addition should be that the reaction solution does not exceed -40°C, and react for 15min , then 7-octen-1-ol (compound 3) (8.68g, 67.81mmol) was diluted with 20ml of dichloromethane, and then added dropwise to the reaction solution. The rate of addition should not exceed -60°C. After reacting for 1h, add 60ml of triethylamine, stir at -78°C for 15min, the reaction solution gradually rises to room temperature, then add 60ml of water, separate the organic phase with a separatory funnel, and extract the aqueous phase with ethyl ...

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Abstract

This invention relates to a complete synthesis means of ( 2R, 3S) - epoxy - 9 - octylene - 1 - alcohol. The invention takes cheap petroleum product 1, 7 - octadiene as raw material, through alkene boron hydrogenation and oxygenation, alcoholic oxygenation, Horner - Wadsworth-Emmons reaction, ester reduction Sharpless epoxidation five steps reaction, then synthesize the ( 2R, 3S) - epoxy - 9 - octylene - 1 - alcohol which has good selectivity, low cost and high yield.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a total synthesis method of a natural product intermediate (2R, 3S)-epoxy-9-octen-1-ol. Background technique [0002] In recent years, many active ingredients have been isolated from ginseng and other plants, and their structures are as follows: [0003] [0004] Due to the low content of these active substances in plants, the extraction process is complex and cumbersome, and it is difficult to obtain a large amount and carry out subsequent animal experiments and clinical studies, so total synthesis has become an inevitable way, (2R, 3S)-epoxy-9- Octen-1-ol is a common intermediate in the synthesis of these natural products, and so far no report has been found on the total synthesis of this important intermediate. Contents of the invention [0005] In order to solve the deficiencies in the above-mentioned prior art, the object of the present invention is to pro...

Claims

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Application Information

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IPC IPC(8): C07D303/14C07D301/03
Inventor 哈成勇王广军沈敏敏
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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