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Preparation method with four-step synthesis of 28-homobrassinolide

A technology of steroid lactone and four-step method, which is applied in the field of preparation of four-step synthesis of 28-homobrasinolide, can solve the problems of high preparation cost, large environmental pollution, and difficult industrial production, and achieves a simple and environmentally friendly method , the effect of a wide range of sources

Active Publication Date: 2018-11-02
JIANGXI AGRICULTURAL UNIVERSITY +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The object of the present invention is to provide a kind of green environmental protection, pollution-free, environment-friendly, raw material is easy to obtain, source is extensive, cost is low, method is simple, is suitable for the preparation method of industrialized production four-step synthetic 28-homobrasinolide, the The preparation method solves the problems of high preparation cost, large environmental pollution and difficulty in industrial production in the prior art

Method used

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  • Preparation method with four-step synthesis of 28-homobrassinolide
  • Preparation method with four-step synthesis of 28-homobrassinolide

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Effect test

Embodiment 1

[0027] (2, 22)-diene-24S-ethyl-5α-cholestan-6-one (410.67 g, 1.00 mol), potassium persulfate (152.00 g, 1.00 mol), fructose ketone (254.32 g , 1.00 mol), water (2 L) were placed in a three-neck flask, and stirred at 25 °C for 5 h. Add ethyl acetate, wash with water, dry, and recover ethyl acetate to obtain product 1: (2 α, 3 α,22 R, 23 R) - 2, 3, 22, 23 - Diepoxy- 24 S - ethyl - 5α-cholestan-6-one. Transfer (2α, 3 α, 22 R, 23 R) - 2, 3, 22, 23 - Diepoxy- 24 S - Ethyl - 5 α - Cholesta-6 -one to a three-neck flask, and add four Butylammonium bromide (32.24 g, 0.10 mol) and water (2 L), at 25 ℃, feed carbon dioxide until the reaction is complete. Add ethyl acetate, wash with water, dry, recover ethyl acetate to obtain product 2: (2 α, 3 α,22 R, 23 R) - 2, 3, 22, 23 - dicarbonate - 24 S - ethyl - 5α-cholestan-6-one. Transfer (2 α, 3 α, 22 R, 23 R) - 2, 3, 22, 23 - dicarbonate - 24 S - ethyl - 5 α - cholestan-6-one to a three-necked flask, and add m-Chloroperbenzoic acid (172....

Embodiment 2

[0029] (2, 22)-diene-24S-ethyl-5α-cholestan-6-one (410.67 g, 1.00 mol), 50% hydrogen peroxide (68.00 g, 1.00 mol), fructose ketone (254.32 g , 1.00 mol), water (2 L) were placed in a three-neck flask, and stirred at 25 °C for 5 h. Add ethyl acetate, wash with water, dry, and recover ethyl acetate to obtain product 1: (2 α, 3α, 22 R, 23 R) - 2, 3, 22, 23 - Diepoxy- 24 S - ethyl- 5 alpha-cholestan-6-one. Transfer (2 α, 3 α, 22 R, 23 R) - 2, 3, 22, 23 - Diepoxy- 24 S - Ethyl - 5 α - Cholester-6-one to a three-neck flask, and add Tetrabutylammonium bromide (32.24 g, 0.10 mol) and water (2 L), at 25 ℃, feed carbon dioxide until the reaction is complete. Add ethyl acetate, wash with water, dry, recover ethyl acetate to obtain product 2: (2 α, 3 α,22 R, 23 R) - 2, 3, 22, 23 - dicarbonate - 24 S - ethyl - 5α-cholestan-6-one. Transfer (2 α, 3 α, 22 R, 23 R) - 2, 3, 22, 23 - dicarbonate - 24 S - ethyl - 5 α - cholestan-6-one to a three-necked flask, and add m-Chloroperbenzoic acid ...

Embodiment 3

[0031] (2, 22)-diene-24S-ethyl-5α-cholestan-6-one (410.67 g, 1.00 mol), potassium persulfate (152.00 g, 1.00 mol), quinidinone ( 324.42 g, 1.00 mol), water (2 L) were placed in a three-necked flask, and stirred at 25 °C for 5 h. Add ethyl acetate, wash with water, dry, and recover ethyl acetate to obtain product 1: (2 α, 3α, 22 R, 23 R) - 2, 3, 22, 23 - Diepoxy- 24 S - ethyl- 5 alpha-cholestan-6-one. Transfer (2 α, 3 α, 22 R, 23 R) - 2, 3, 22, 23 - Diepoxy- 24 S - Ethyl - 5 α - Cholester-6-one to a three-neck flask, and add Tetrabutylammonium bromide (32.24 g, 0.10 mol) and water (2 L), at 25 ℃, feed carbon dioxide until the reaction is complete. Add ethyl acetate, wash with water, dry, recover ethyl acetate to obtain product 2: (2 α, 3 α,22 R, 23 R) - 2, 3, 22, 23 - dicarbonate - 24 S - ethyl - 5α-cholestan-6-one. Transfer (2 α, 3 α, 22 R, 23 R) - 2, 3, 22, 23 - dicarbonate - 24 S - ethyl - 5 α - cholestan-6-one to a three-necked flask, and add m-Chloroperbenzoic acid (1...

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Abstract

The invention discloses a preparation method with four-step synthesis of 28-homobrassinolide, which takes (2,22)-diene-24S-ethyl-5alpha-cholest-6-ketone as a raw material, and 28-homobrassinolide is obtained from epoxidation, esterification, Baeyer-Villiger oxidation and hydrolysis reaction, the preparation method provided by the invention has the advantages of green environmental protection, no pollution, environment friendliness, easily available raw materials, wide source, low cost, simple method and suitability for industrial production, and the preparation method solves the problems of high preparation cost and difficulty in industrial production in the prior art.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a preparation method for synthesizing 28-homobrassinolide in four steps. Background technique [0002] Brassinolide is a new green and environmentally friendly plant growth hormone that is harmless to humans and animals and non-toxic. In 1979, American scientist Grove (Grove M.D. et al . Nature (London, United Kingdom), 1979, 281(5728): 216 - 217) is a hormone isolated from rape pollen, and through the identification of its crystals, its structure is confirmed to be a sterol compound, called For brassinolide. Brassinolide is the latest plant growth regulator discovered in nature, known as the sixth type of plant growth regulator, its biological activity far exceeds the existing five major hormones (auuxin, gibberellin, cytokinin, abscisic acid and vinyl). There are more than 40 kinds of brassinolide analogues that have been found so far, but few of them have high biological a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00
CPCC07B2200/07C07J73/003
Inventor 黄建平程丽黄芮官莹莹吴忆蕾方文超赖粮川李倩
Owner JIANGXI AGRICULTURAL UNIVERSITY
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