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Synthesis method of 28-homobrassinolide

A synthesis method and a technology for sterolide, which are applied in the fields of botanical equipment and methods, steroids, chemicals used for biological control, etc., can solve the problems of complicated operation, low yield, pollute the environment, etc., and achieve a synthesis method. Simple, simple process, and the effect of reducing production costs

Active Publication Date: 2021-05-28
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has high academic value, but the reaction steps are long, the operation is complicated, the yield is low, and it has no industrial production value
[0005] Since the content of brassinolide series compounds extracted from natural plants is very small, and the purity of the extracted products is not high, it is difficult to meet the needs of research and application
Most of the current synthesis methods use expensive and highly toxic osmium tetroxide as the oxidant, which increases the cost and pollutes the environment

Method used

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  • Synthesis method of 28-homobrassinolide
  • Synthesis method of 28-homobrassinolide
  • Synthesis method of 28-homobrassinolide

Examples

Experimental program
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Embodiment 1

[0036](1) (5,22) - Preparation of diene-3-methylsulfyl ester (C)

[0037]In an ice bath at 3 ° C, 8.2 g (20 mmol) of elthyl alcohol was dissolved in 100 ml butanone, 6.2 ml (4.04 g, 40 mmol) triethylamine was added. Under stirring, 3.44 g (30 mmol) of toluenesulfonyl chloride was slowly added dropwise, and the reaction was continued for 1 h. TLC dotted tracks, after completion of the reaction, 40 ml of NaCl solution was quenched. The standing hierarch is divided into the upper organic phase, and the organic phase sequentially uses 40ml NaHCO.3The solution was washed twice with 100 mL of water. The organic phase was poured into a beaker with 800 ml of ice water, stirred for 20 min, put it into the refrigerator crystallization for 15 min, filtered, filter cake was washed with ice water, and the filter cake was placed in an oven to dry, 9.53 g of intermediate C ( 5,22) - Dienne-3-methylsulfamatide crude, yield 97%.

[0038](2) Preparation of 22E-Intene-3α, 5-ring-5α cholester-6-alcohol (D)

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Embodiment 2

[0051]Example 2 was the same as that of the first embodiment, and the preparation of 22E-lyne-3α, 5-ring -5α cholester-6-alcohol (D): the resulting 4.90 g (10 mmol) intermediate C is dissolved in 100 mL of acetone, add 20 ml of water and 1.84 g (10 mmol) kHCO to the flask.3Heated at 75 ° C to reflux, reaction for 5 h. The TLC point plate tracking, after the reaction is complete, cool down, stand in the hierarchy, and separate the organic phase. The organic phase was washed twice with 40ml NaCl; then, with anhydrous NaHSO4Dry, filtered, vacuum yarn. The crude product was separated by column chromatography. The intermediate 22e-olene-3α, 5-ring-5α cholester-6-alcohol 3.07 g, yield of 78%.

Embodiment 3

[0053]Example 3 is the same as that of the preparation method of Example 1, and the preparation of 22E-anne-3α, 5-ring-5α cholester-6-alcohol (D): the resulting 4.90 g (10 mmol) intermediate C is dissolved in 100 ml of acetone, add 20 ml of water and 2.45 g (20 mmol) Na to the flask.2CO3Heated at 75 ° C to reflux, reaction for 5 h. The TLC point plate tracking, after the reaction is complete, cool down, stand in the hierarchy, and separate the organic phase. The organic phase was washed twice with 40ml NaCl; then, with anhydrous NaHSO4Dry, filtered, vacuum yarn. The crude product was separated by column chromatography. The intermediate 22e-olene-3α, 5-ring-5α cholester-6-alcohol 2.98 g, yield of 75%.

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Abstract

The invention discloses a synthesis method of 28-homobrassinolide, which comprises the steps of selecting stigmasterol B as an initial raw material, carrying out esterification reaction to obtain a compound C, and heating and refluxing the compound C under an alkaline condition to obtain a compound D; oxidizing the compound D to obtain a compound E; performing oxidation and ring opening on the compound E to obtain a compound F; carrying out a dihydroxylation reaction on the compound F to obtain a compound G; and carrying out oxidation rearrangement reaction on the compound G to obtain a compound A 28-homobrassinolide. The brand new synthesis of 28-homobrassinolide is realized through a simple six-step synthesis process including esterification reaction, ring-closing reaction, oxidation reaction, oxidation ring-opening reaction, dihydroxylation reaction and oxidation rearrangement reaction, and the preparation method has the advantages of easily available raw materials, short synthesis route, relatively ideal yield, low cost, low toxicity, low environmental pollution and the like, has a high industrial production value and a good agricultural application prospect, and provides a new path for synthesis of a steroid plant growth regulator 28-homobrassinolide substance.

Description

Technical field[0001]The present invention belongs to the art of organic synthesis, involving a synthesis and preparation method of steroidal plant growth regulators - 28-hypotransolactone.[0002]technical background[0003]Brassicide is a new type of green environmentally friendly plant growth regulator. In 1970, American scientist Grove separated from rapeseed pollen, by research on its crystallization structure, found that this is a sterol-based compound, referred to as laminin lanes. This is one of the latest plant growth regulators in nature, called sixth type of plant hormones. Depending on the molecular structure and biological activity, the lantide in the laminin is: 24-mixed laminate; 24-histone tsolane; 28-high metropolin lactone; 28-high prolitone . 28-hyperobus lactone has the highest biological activity, and is the only plant hormone that is currently highly active for single, double-stranded leaves and wooden undergraduate plants.[0004]Japan's MORI et al. Takes the renova...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00A01N43/22A01P21/00
CPCC07J73/003A01N43/22Y02P20/55
Inventor 黄和张幸纪元沈宝星林雅玫马成功易香羽
Owner NANJING NORMAL UNIVERSITY
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