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Manufacture method of ethyl brassinolide

A technology of ethyl brassinolide and ethyl, applied in the field of chemistry, can solve the problems of inability to realize industrialized production, low yield of the final product, expensive, etc., and achieves the advantages of improving yield, shortening reaction time, and improving production efficiency. Effect

Inactive Publication Date: 2008-05-14
浙江来益生物技术有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses expensive and highly toxic osmium tetroxide, and the yield of the final product is low, so industrial production cannot be realized

Method used

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  • Manufacture method of ethyl brassinolide
  • Manufacture method of ethyl brassinolide
  • Manufacture method of ethyl brassinolide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] [Example 1] Preparation of ethyl brassinolide

[0049] 1. Preparation of compound 2,22-diene-5α-stigmaster-6-one

[0050] Starting from stigmasterol, through the method of literature Chem.Pharm.Bull., 1982, 30 (11), pp4181-4185., through four-step reaction, directly obtain 2,22-diene-5α-stigmaster-6-one .

[0051] 2. Preparation of compound 2α, 3α, 22R, 23R-tetrahydroxy-5α-stigmaster-6-one

[0052] In a 3000ml three-neck flask, add 100g of 2,22-diene-5α-stigmaster-6-one, add ligand: 20g of phenanthrene-dihydroquinidine ether, stir and dissolve with 2000ml of tert-butanol, and cool to 0 ℃, slowly dropwise add 300ml of the oxidant ruthenium tetroxide prepared according to the example, keep the dropping temperature below 0℃, and then react at 0℃ for 1 hour; then at 0℃, slowly add 200g of sodium bisulfite to end the reaction. The reaction solution was dispersed in 2000ml water, extracted three times with 1000ml ethyl acetate respectively, the ethyl acetate layers were co...

Embodiment 2

[0059] [embodiment 2] the preparation of ethyl brassinolide

[0060] 1. Preparation of compound 2,22-diene-5α-stigmaster-6-one

[0061] Starting from stigmasterol, through the method of literature Chem.Pharm.Bull., 1982, 30 (11), pp4181-4185., through four-step reaction, directly obtain 2,22-diene-5α-stigmaster-6-one .

[0062] 2. Preparation of compound 2α, 3α, 22R, 23R-tetrahydroxy-5α-stigmaster-6-one

[0063] In a 3000ml three-necked flask, add 90 g of 2,22-diene-5α-stigmaster-6-one, and 2α, 3α-dihydroxy-5α-(22E)-en-6-one recovered in Example 1 10g, add ligand: 20g of phenanthrene-dihydroquinidine ether, stir and dissolve with 2000ml of tert-butanol, cool to -5°C, slowly add 300ml of oxidant ruthenium tetroxide dropwise, keep the dropping temperature less than -5°C, and then in React at -5°C for 1 hour; then at 0°C, slowly add 220 g of sodium bisulfite to end the reaction. The reaction solution was dispersed in 2000ml of water, extracted three times with 1000ml ethyl ac...

Embodiment 3

[0070] [embodiment 3] the preparation of ethyl brassinolide

[0071] 1. Preparation of compound 2,22-diene-5α-stigmaster-6-one

[0072] Starting from stigmasterol, through the method of literature Chem.Pharm.Bull., 1982, 30 (11), pp4181-4185., through four-step reaction, directly obtain 2,22-diene-5α-stigmaster-6-one .

[0073] 2. Preparation of compound 2α, 3α, 22R, 23R-tetrahydroxy-5α-stigmaster-6-one

[0074] In a 10000ml three-neck flask, add 250g of 2,22-diene-5α-stigmaster-6-one, and 50g of recovered 2α,3α-dihydroxy-5α-(22E)-en-6-one, and add Body: 60g of phenanthrene-dihydroquinidine ether, stirred and dissolved with 2000ml of tert-butanol, cooled to -15°C, slowly added dropwise 900ml of oxidant ruthenium tetroxide prepared according to Example 1, keeping the dropping temperature below -10°C, Then react at -10°C for 1 hour; then at 0°C, slowly add 220g of sodium bisulfite to end the reaction. The reaction solution was dispersed in 6000ml water, extracted three times...

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Abstract

The invention discloses a new preparing method of ethyl brassin lactone, which comprises the following steps: 1) preparing intermediate compound of 2, 22- diene -5a-stigma-6-ketone according to present technology; 2) adopting ruthenium tetroxide as oxidant, phenanthrene dihydrochinidin ether as ligand to control stereoscopic structure; proceeding asymmetric double-hydroxide for 2, 22-diene-5a- stigma-6-ketone to generate 2a, 3a, 22R, 23R-tetrahydroxy-5a- stigma-6-ketone; 3) making 2a, 3a, 22R, 23R-tetrahydroxy-5a- stigma-6-ketone to produce acetylate through acetylate protection; 4) using peroxyformic acid as agent to proceed Baeyer-Villiger reaction; lactonizing the acetylate to produce lactone: 2a, 3a, 22R, 23R-tetraace oxygen base-24S- ethyl group-B-high-7- oxa-5a-cholester-6-ketone; hydrolyzing the lactone to produce ethyl brassin lactone.

Description

technical field [0001] The invention relates to a method for preparing plant hormones, in particular to a method for preparing ethyl brassinolide, and belongs to the field of chemistry. Background technique [0002] Before 1970, the plant growth hormones that have been discovered can be divided into five categories: auxin, gibberellin, hexene, abscisic acid and cytokinin. In 1970, Mitchll, a research center of the US Department of Agriculture, isolated a seven-membered ring compound with a steroidal skeleton called brassinolide from rape pollen. It has very strong physiological activity, at very low concentration (10 -9 g / ml) can significantly promote plant cell growth and division, thereby regulating plant growth and development. It exists in a variety of plants, which can enhance the cold resistance, disease resistance, salt resistance and weed resistance of crops, and play a role in comprehensively regulating plant growth. In the past, the existence of steroidal plant ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J73/00C07J9/00
Inventor 陈鹏袁建勇金一平叶伟东张定丰
Owner 浙江来益生物技术有限公司
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