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A technology of epibrasinolides and compounds, which is applied in the field of preparation of plant growth regulators, can solve the problems of complicated operations, many reaction steps, and high toxicity of reagents, and achieve the effects of convenient operation, low toxicity, and low pollution
Inactive Publication Date: 2010-08-25
SHANGHAI VEGCIDES BIO FARM NANCHANG
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However, when we repeated this experiment, we found that the reaction situation was not ideal, the impurity content was high, and the experimental operation was very complicated
It can be seen that the current reports on the laboratory synthesis me
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[Example 1]
The sulfonylation of ergosterol.
Dissolve ergosterol (200g, 0.50mol) in 1.0 liter of anhydrous pyridine, lower the temperature to -5~10℃, and slowly add dropwise the pyridine solution of methanesulfonyl chloride (100g, 0.55mol, dissolved in 200mL of anhydrous pyridine) . Stir the reaction below 15°C for 3 to 4 hours. After the reaction is complete, pour the reaction solution into a heated stirring ice salt water bath, and a large amount of solids are precipitated. After standing for a period of time, pour the supernatant liquid, and then rinse it with ice salt water, let it stand, pour the supernatant liquid, and then pump the material After filtering, washing with water and drying, 290g of sulfonylated ergosterol was obtained. The yield was 104%.
b. Use catalytic amount of osmium tetroxide as oxidant, and use one of meta-chloroperoxybenzoic acid, morpholine peroxide, sodium bromate, tert-butyl hydroperoxide, and hydrogen peroxide as co-oxidant, compound 3 The hydroxyl group in oxidized to carbonyl group to obtain compound 4.
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Abstract
The invention relates to a preparation method of a plant growth regulator, in particular to a preparation method of 24-epibrassinolide, which belongs to the chemical field, and comprises the following steps that: 1. starting from ergosterol 1, an intermediate body 3 is prepared through two reactions, i.e. methyl sulfonyl and hydrolysis according to a traditional synthesis process; 2. the intermediate body 3 is oxidized by a novel oxidation system osmium tetroxide/inter-chloro benzoic acid peroxide to prepare an intermediate body 4; and 3. the intermediate body 4 is finally converted into the 24-epibrassinolide 8 through four reactions, i.e. reduction, rearrangement, dihydroxylation and lactonization according to the traditional synthesis process. Compared with the traditional oxidation system chromium trioxide/pyridine used in the oxidization of the intermediate body 3 into the intermediate body 4, the novel oxidation system used by the invention has the advantages of convenient operation and little pollution, and is more applicable to industrial production.
Description
Technical field The invention relates to a preparation method of a plant growth regulator, especially a preparation method of 24-epibrassinolide. It belongs to the field of chemistry. Background technique In 1979, Crove and others of the Research Institute of the United States Department of Agriculture extracted a compound with a steroidal skeleton structure from rape pollen, which was later named Brassinolide (Brassinolide, also called brassinolide) (MD Grove, GFSpencer, WK Rohwedder, N. Mandava, JF Worley, JD Warthen, Jr., GL Steffens, JLFlippen-Anderson, and JCCook, Jr., Nature (London), 1979, 281, 216). It has a very strong physiological activity, at very low concentrations (10 -9 G / L) shows a significant function of promoting plant growth and development. So far, people have isolated nearly 60 kinds of brassinolide from plants. Among them, brassinolide, 24-epibrassinolide and 28-homobrassinolide are the three most active. 24-Epibrassinolide is the first sterol compound...
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