Reductive composition for preparing 24-epibrassinolide

A kind of technology of epibrassinolide and composition, applied in the field of reducing composition for preparing 24-epibrassinolide, can solve the problems of non-reaction, low product yield and the like

Active Publication Date: 2012-09-12
江西威敌生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when we applied these conditions to the reduction reaction of intermediate 4, we failed to obtain ideal experimental results, either no reaction, or the product yield was very low

Method used

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  • Reductive composition for preparing 24-epibrassinolide
  • Reductive composition for preparing 24-epibrassinolide
  • Reductive composition for preparing 24-epibrassinolide

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preparation example Construction

[0024] A novel oxidation-free low-temperature preparation method of 24-epibrassinolide, comprising the following steps:

[0025] According to the existing synthesis process, starting from raw material 1, it is prepared in three steps Figure 5 The first compound 3 shown.

[0026] b. The first compound 3 is oxidized with [Ru]-air to Image 6 The second compound shown in 4

[0027] c. The second compound 4 and Li-R 1 (CH 2 ) n R 2 The reducing system of the composition reacts at 0-80°C

[0028] transform into Figure 7 The third compound 5 shown.

[0029] d. The third compound 5 is prepared by rearrangement, dihydroxylation and lactonization according to the existing synthesis process Figure 8 The final product 24-epibrassinolide 8 is shown.

[0030] The synthesis of the first compound (also called the first intermediate) 3 into the second compound (also called the second intermediate) 4 was carried out using a novel recyclable ruthenium catalyst in water under air ox...

Embodiment 1

[0054] Sulfonylation of ergosterol:

[0055] like figure 1 As shown, dissolve ergosterol (200g, 0.55mol) in 1.0 liter of anhydrous pyridine, cool down to -5~10°C, slowly add a solution of methanesulfonyl chloride in pyridine (100g, 0.55mol. Dissolve in 200mL of anhydrous in pyridine). After the reaction is completed, the reaction solution is poured into a vigorously stirred ice-salt water bath, and a large amount of solids are precipitated. After standing for a period of time, the supernatant is poured out, and then rinsed once with ice-salt water. After standing, the supernatant is poured out, and then the The material was suction filtered, washed with water, and dried to obtain 290 g of sulfonylated ergosterol, with a yield of 104%.

[0056] 1 H NMR (400M Hz, CDCl 3 )δ0.63(3H, s, 18-H), 0.82(3H, d, J=6.9Hz, 26-H), 0.84(3H, d, J=6.9Hz, 27-H), 0.92(3H, d, J=6.9Hz, 28-H), 0.96(3H, s, 19-H), 1.04(3H, d, J=6.9Hz, 21-H), 1.22-2.15(20H, m), 3.02( 3H, s, SO 2 CH 3 ), 4.63(1...

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Abstract

The invention discloses a reductive composition for preparing 24-epibrassinolide, which is applicable to an oxidizing step in preparation of the 24-epibrassinolides. The reductive composition comprises metal lithium and one or more of R1(CH2)nR2 compounds, wherein n is equal to 2-6; R1 is OH or NH2; and R2 is NH2 or OH.

Description

Technical field: [0001] The invention relates to the field of chemistry, and relates to a method for preparing a plant growth regulator, in particular to a reducing composition for preparing 24-epibrassinolide. Background technique: [0002] In 1979, Crove et al. from a research institute affiliated to the U.S. Department of Agriculture extracted a compound with a steroidal skeleton structure from rapeseed pollen, which was later named Brassinolide (also known as brassinolide) (M.D. Grove, G.F. Spencer, W.K. Rohwedder, N. Mandava, J.F. Worley, J.D. Warthen, Jr., G.L. Steffens, J.L. Flippen-Anderson, and J.C. Cook, Jr., Nature (London), 1979, 281, 216). It has extremely strong physiological activity, at very low concentrations (10 -9 g / L) has shown the obvious function of promoting plant growth and development. So far, nearly 60 kinds of brassinolides have been isolated from plants. Among them, brassinolide, 24-epibrasinolide and 28-homobrasinolide are the three most activ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00
Inventor 吴中兴
Owner 江西威敌生物科技有限公司
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