Preparation method of 25-hydroxyl-7-dehydrocholesterol

A technology of dehydrocholesterol and triene cholesterol, applied in the direction of steroids, organic chemistry, etc., can solve problems such as difficult industrialization, excessive mercury content, and major environmental protection problems, and achieve cost reduction of three wastes, good reaction selectivity, The effect of simple process

Inactive Publication Date: 2017-06-13
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned methods all have their own shortcomings. In the method (a), a highly toxic mercury-containing reagent is used, which has a relatively large environmental protection problem, and the mercury content in the product is easily caused to exceed the standard, and the industrialization is relatively difficult.
In the method (b), the yield of the last step of epoxy ring opening is low, only 70%, and the total yield is only about 50%

Method used

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  • Preparation method of 25-hydroxyl-7-dehydrocholesterol
  • Preparation method of 25-hydroxyl-7-dehydrocholesterol

Examples

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Effect test

Embodiment 1

[0026] Example 1 According to the preparation method of the present invention, 25-hydroxy-7-dehydrocholesterol was prepared.

[0027] 1) Protection of the 3-position hydroxyl group to obtain intermediate compound Ⅱ

[0028] At room temperature (25°C), dissolve 3.82 g (10 mmol) of 5,7,24-triene cholesterol in 40 ml

[0029] In dichloromethane, add 0.06g (0.5mmol) DMAP, 2.04g (20mmol) acetic anhydride, 3.03g

[0030] (30mmol) triethylamine, stirred and reacted at room temperature for 3h, after TLC traced the complete reaction, added 15ml10%

[0031] Dilute hydrochloric acid layered to remove the water phase, the organic phase was washed with 15ml of water and layered, and the organic phase was dried with anhydrous sodium sulfate

[0032] Filtration and concentration gave a pale yellow crude product, which was recrystallized from methanol to obtain 3.89 g of intermediate compound II with a yield of 91.6% and a melting point of 82-84°C. 1 H NMR (400 MHz, CDCl 3 ) δ 5.56 (m, 1H...

Embodiment 2

[0041] According to the method in step 1) of Example 1, the only difference is that acetic anhydride is replaced by benzoic anhydride, and the molar ratio of 5,7,24-triene cholesterol, protective reagent, catalyst, and acid-binding agent is adjusted to 1:1.5: 0.01:1.5, other operations are the same as step 1), and the yield of intermediate II is 84.5%.

Embodiment 3

[0043] According to the method in step 1) of Example 1, the only difference is that acetic anhydride is replaced by acetyl chloride, and the molar ratio of 5,7,24-triene cholesterol, protective reagent, catalyst, and acid-binding agent is adjusted to 1:3:0.06 : 5, other operations are the same as step 1), and the yield of intermediate II is 94.5%.

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Abstract

The invention discloses a preparation method of 25-hydroxyl-7-dehydrocholesterol. The preparation method takes 5,7,24-trienecholesterol as a raw material; 3-site hydroxyl of the raw material is protected to prepare an intermediate compound II; the intermediate compound is subjected to D-A protection reaction of diene to obtain an intermediate compound III; the intermediate compound III is subjected to double-bond halogenation and hydroxylation reaction to obtain an intermediate compound IV; the intermediate compound IV is subjected to de-protection and debromination reaction to prepare the 25-hydroxyl-7-dehydrocholesterol. By adopting the method provided by the invention, the 25-hydroxyl-7-dehydrocholesterol is obtained; compared with a preparation method reported in existing literature reports, the product yield is high and the purity is good; the reaction selectivity is relatively good and reaction operation is simple; pollution caused by a mercury-containing toxic and harmful reagent is effectively avoided; the cost of three wastes is reduced and the preparation method is suitable for industrialized popularization and application.

Description

technical field [0001] The invention provides a 25-hydroxyvitamin D 3 Preparation method of important intermediate 25-hydroxyl-7-dehydrocholesterol. Background technique [0002] 25-hydroxy-7-dehydrocholesterol is the synthetic 25-hydroxyvitamin D 3 An important raw material, 25-hydroxyvitamin D 3 is vitamin D 3 Active metabolites in animals, relative to vitamin D 3 With stronger activity, it can bypass liver metabolism and be directly absorbed by humans or animals. In addition to regulating calcium and phosphorus metabolism in the body, it is also widely used in feed additives to promote the bone development of poultry animals. In addition, it can also regulate the immune function of the human body and reduce the occurrence of osteoporosis, so its market prospect is very promising. [0003] Before the present invention, the existing methods for preparing 25-hydroxy-7-dehydrocholesterol were mainly through: (a) mercury hydroxylation reduction (Zhurnal Organiccheskoi Kh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/00
Inventor 金灿苏为科孙彬
Owner ZHEJIANG UNIV OF TECH
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