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A kind of preparation method of 28-homobrasinolide

A technology of lactone and intermediate, which is applied in the field of preparation of 28-homobrassinolide, can solve the problems of complicated operation, difficult separation of products, pollution and the like

Active Publication Date: 2020-07-07
郑州万牛生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In the current synthesis method, the oxidant is expensive and highly toxic osmium tetroxide, and the stereoselectivity of dihydroxylation of olefins is not high, resulting in high cost and serious pollution; the amount of chiral catalyst is large, or it is difficult to separate from the product and cannot be reused. As a result, problems such as high cost and cumbersome operation have greatly limited its application.

Method used

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  • A kind of preparation method of 28-homobrasinolide
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  • A kind of preparation method of 28-homobrasinolide

Examples

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Effect test

Embodiment 1

[0031] Add (2,22)-diene-24S-ethyl-5α-cholest-6-one (410.67g, 1mol), Cat 1 (0.5mol%), water in a reactor equipped with a thermometer and a stirrer (830ml), add hydrogen peroxide (37.41g) under stirring at 0°C, TLC detects that the reaction is complete, extract with dichloromethane, wash with saturated brine, recover dichloromethane to obtain 404.16g of intermediate b for use, with a yield of 91.3%. Intermediate b (404.16g), TBAB / GO (32.6g) and water (1210ml) were sequentially added to the reactor, carbon dioxide was introduced at room temperature until the reaction was complete, TBAB / GO was recovered by centrifugal separation, and washed with water to obtain intermediate c (410.75g) for use, yield 86.0%. Put the obtained intermediate c and water (1230ml) into the reactor, slowly add m-chloroperoxybenzoic acid (134.6g) at 10°C, stir at room temperature for 40min, wash with water, extract with dichloromethane, recover the dichloromethane to obtain the intermediate d is ready for ...

Embodiment 2

[0033] Add (2,22)-diene-24S-ethyl-5α-cholester-6-one (410.67g, 1mol), Cat 1 (0.1mol%), water in a reactor equipped with a thermometer and a stirrer (1640ml), hydrogen peroxide (41.1g) was added with stirring at 0°C, TLC detected until the reaction was complete, extracted with dichloromethane, washed with saturated brine, and recovered dichloromethane to obtain 395.75g of intermediate b for use with a yield of 89.4%. Intermediate b (395.75g), TBAB / GO (39.6g) and water (1980ml) were sequentially added to the reactor, carbon dioxide was introduced at room temperature until the reaction was complete, TBAB / GO was recovered by centrifugation, and washed with water to obtain intermediate c (401.7g) for use, yield 84.7%. Put the obtained intermediate c and water (1500ml) into the reactor, slowly add m-chloroperoxybenzoic acid (130.6g) at 10°C, stir at room temperature for 40min, wash with water, extract with dichloromethane, recover the dichloromethane to obtain the intermediate d is ...

Embodiment 3

[0035] Add (2,22)-diene-24S-ethyl-5α-cholest-6-one (410.67g, 1mol), Cat 2 (0.3mol%), water in a reactor equipped with a thermometer and a stirrer (1230ml), hydrogen peroxide (132.2g) was added under stirring at 30°C, TLC detected until the reaction was complete, extracted with dichloromethane, washed with saturated brine, recovered dichloromethane to obtain 370.7g of intermediate b for use, with a yield of 83.0%. Intermediate b (401.1g), TBAB / GO (80.2g) and water (4010ml) were sequentially added to the reactor, carbon dioxide was introduced at 50°C until the reaction was complete, TBAB / GO was recovered by centrifugal separation, and washed with water to obtain intermediate c (423.6g) for use, the yield was 88.1%. Put the obtained intermediate c and water (2000ml) into the reactor, slowly add m-chloroperoxybenzoic acid (137.7g) at 10°C, stir at room temperature for 40min, wash with water, extract with dichloromethane, recover the dichloromethane to obtain the intermediate d is ...

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Abstract

The invention relates to a preparation method of 28-homobrassinolide, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: preparing a corresponding asymmetric epoxide from (2,22)-diene-24S-ethyl-5alpha-cholest-6-one under the action of a chiral catalyst and an oxidizing agent, and then carrying out esterification, oxidation and hydrolysisreactions to obtain a product. The catalyst provided by the invention has the advantages of high selectivity, high efficiency, and low dosage, and the method has advantages of low cost, simple process, convenient operation, environmental protection and good industrial application value.

Description

Technical field [0001] The invention relates to a method for preparing 28-homobrassinolide, which belongs to the technical field of organic synthesis. Background technique [0002] Brassinolide is a plant growth promoter. It was isolated for the first time by the staff of the US Department of Agriculture in 1979. It exhibits activity at the nanogram / single plant level, which is several orders of magnitude lower than other known types of plant growth promoters. There are more than 40 brassinolide analogues that have been discovered, but only four or five have high biological activity and practical value, and they have been artificially synthesized, such as BR in the United States, Epi BR and Japan Homo BR et al. (Study on the synthesis process of 28-homobrassinolide [D]. Huang Binrong, Nanchang University, 2015). It is reported that brassinolide significantly increases the yield of several commercially important crops even at very low dose levels (ACS Symposium Series 474; Ameri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J73/00
CPCC07J73/003
Inventor 蒋德刚李文博韩虎峰
Owner 郑州万牛生物技术有限公司
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