Method for synthesizing 16beta,21-epoxy-20S-methyl-alkene-3beta,21beta-pregnane-diol

An epoxidation reaction and compound technology, applied in the direction of steroids, organic chemistry, etc., to achieve the effect of good stereochemical selectivity, convenient operation and mild reaction conditions

Inactive Publication Date: 2012-11-14
EAST CHINA UNIV OF SCI & TECH +1
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  • Description
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Problems solved by technology

But so far there is no report on the chemical synthesis of 16β, 21-epoxy-20S-methyl-5-ene-3β, 21β-pregna-diol

Method used

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  • Method for synthesizing 16beta,21-epoxy-20S-methyl-alkene-3beta,21beta-pregnane-diol
  • Method for synthesizing 16beta,21-epoxy-20S-methyl-alkene-3beta,21beta-pregnane-diol
  • Method for synthesizing 16beta,21-epoxy-20S-methyl-alkene-3beta,21beta-pregnane-diol

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Embodiment

[0016] 3β-tert-butyldimethylsilyloxy-16α, 17α-epoxy-5-ene-20-progesterone (Compound 3) Preparation:

[0017] In a 1000ml reaction flask, add raw compound 2, 30g (91.5mmol) and 600ml of methanol, stir, and at 0°C to 5°C, add an aqueous solution of NaOH (9.6g of NaOH dissolved in 60ml of water), 120ml of H 2 o 2 , the system was cloudy, and reacted for 7 hours at 0°C to 25°C, the raw materials disappeared, and the reaction was stopped. Pour the reaction night into 900ml of water, let stand overnight, filter with suction, and dry to obtain 26.7g of crude epoxidized product with a yield of 96%. Melting point: 174.3-177.8°C.

[0018] Dissolve 26.7 g of the obtained epoxidized crude product in 500 ml of dichloromethane, add 14.75 g (97.2 mmol) of tert-butyldimethylsilyl chloride, the system is always clear, add 13.88 g (204.93 mmol) of imidazole, and it becomes turbid. After stirring at room temperature for 18 hours, the reaction was complete. Spin off the dichloromethane liquid...

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Abstract

The invention relates to a method for chemically synthesizing 16beta,21-epoxy-20S-methyl-alkene-3beta,21beta-pregnane-diol, which mainly comprises the following steps of: sequentially carrying out selectivity epoxidation, tertiary butyl dimethylsilyl chloride protection reaction, hydrazine hydrate reduction reaction, manganese dioxide oxidation reaction, nitromethane Michael addition reaction, sodium borohydride reduction reaction and nef reaction on 5,16-diene-pregnant sterol ketone as a raw material to obtain a target. The method for synthesizing 16beta,21-epoxy-20S-methyl-alkene-3beta,21beta-pregnane-diol has advantages of easy raw material preparation, good three-dimension chemical selectivity and special process and is convenient to operate.

Description

technical field [0001] The invention relates to a chemical synthesis method of 16β, 21-epoxy-20S-methyl-5-ene-3β, 21β-pregna-diol. Background technique [0002] Many marine organisms and natural plants contain active ingredients with obvious biological activity, such as polyhydroxy sterols, steroidal saponins, etc. Taking them as drug targets, conducting structure-activity relationship research and structural modification research is one of the important ways to discover new anti-tumor drugs. [0003] 16β, 21-epoxy-20S-methyl-5-ene-3β, 21β-pregna-diol is an important intermediate in the synthesis of antitumor active steroid structure modification. LeThiQuyen; et al, Liebigs Annalen der Chemie 1993. (2), 167-172, reported the degradation of solasodin to obtain this compound. But so far there is no report on the chemical synthesis of 16β, 21-epoxy-20S-methyl-5-ene-3β, 21β-pregna-diol. Contents of the invention [0004] The object of the present invention is to provide a m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00
Inventor 卓超沈平孃郭凤英杜晨捷况丽琴汤秀珍祁双红姚譞丁丹朱云霞
Owner EAST CHINA UNIV OF SCI & TECH
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