Synthetic method of 25-hydroxycholesterol

A technology of hydroxycholesterol and dehydrocholesterol, which is applied in the field of preparation of 25-hydroxycholesterol, can solve the problems of poor selectivity and low yield, and achieve the effects of high selectivity, high yield and environmental friendliness

Active Publication Date: 2015-04-22
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main defect of this method is: selectivity is poor, and yield is relatively low

Method used

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  • Synthetic method of 25-hydroxycholesterol
  • Synthetic method of 25-hydroxycholesterol
  • Synthetic method of 25-hydroxycholesterol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1. A method for preparing 25-hydroxycholesterol, the following steps are carried out in sequence:

[0048] 1) Use 120mL pyridine as solvent, 30mL pyridine (about 0.372mol) as acid binding agent, add 20g 24-dehydrocholesterol (about 0.052mol), 0.2g 4-dimethylaminopyridine (DMAP), drop at room temperature Add 10g (about 0.097mmol) of acetic anhydride (dropped in about 30 minutes). The reaction process was monitored by TLC. After the addition, the reaction was continued at room temperature for 10 hours, and the reaction was completed.

[0049] The reaction liquid is washed with water (50ml×2 water), acid washed (with a volume concentration of 5% dilute hydrochloric acid solution, 50ml×2) and then extracted with dichloromethane (30ml×3), and the extract is used The saturated sodium bicarbonate solution was washed to neutrality, anhydrous sodium sulfate (about 5g) was dried and the solvent (ie, dichloromethane) was removed to obtain 19.1g of acetylated 24-dehydrocholeste...

Embodiment 2

[0056] Example 2. A method for preparing 25-hydroxycholesterol,

[0057] In this embodiment 2, steps 1) and 2) are different from the embodiment 1. The difference lies in:

[0058] 1) Using 100mL of dichloromethane as a solvent, add 20g of 24-dehydrocholesterol (about 0.052mol), 0.2g of DMAP, 10.1g (about 0.1mmol) of triethylamine, and dropwise add 10g (about 0.097mmol) of vinegar at room temperature anhydride. The reaction process was monitored by TLC. After the addition, the reaction was continued at room temperature for 10 hours, and the reaction was completed.

[0059] The reaction solution was washed with dilute hydrochloric acid (volume concentration 5%, 50ml×2), saturated sodium bicarbonate solution (30ml×2), saturated sodium chloride solution (30ml) and dried with anhydrous sodium sulfate (about 5g). The solvent (ie, dichloromethane) was removed by rotary evaporation under reduced pressure (0.1MPa) to obtain 19.0 g of acetylated 24-dehydrocholesterol with a yield of 90.0%. ...

Embodiment 3

[0061] Example 3. A method for preparing 25-hydroxycholesterol,

[0062] In this embodiment 3, steps 1) and 2) are different from the embodiment 1. The difference lies in:

[0063] 1) Using 100mL of dichloromethane as solvent, add 20g of 24-dehydrocholesterol (about 0.052mol), 0.2g of DMAP, 10.1g (about 0.1mmol) of triethylamine, and add 14.1g (about 0.1mol) dropwise at room temperature After the addition of benzoyl chloride, the temperature was raised to reflux (about 40°C), the reaction process was monitored by TLC, and the reaction was completed after refluxing for 24 hours.

[0064] The reaction solution was washed successively with dilute hydrochloric acid, saturated sodium bicarbonate solution, saturated sodium chloride solution and then dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain 23.2 g of benzoylated 24-dehydrocholesterol. The yield was 95.0%.

[0065] 2) Change 0.213g (1.2mmol) of N-bromosuccinimide ...

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Abstract

The invention discloses a synthetic method of 25-hydroxycholesterol. The synthetic method comprises the following steps: (1) protecting 3-hydroxy of 24-dehydrocholesterol so a to obtain acylated 24-dehydrocholesterol; (2) carrying out hydroxyhalogenation reaction on double bonds on the 24th site of the product obtained in the step (1), namely reacting the acylated 24-dehydrocholesterol with deionized water and a halogenated agent for 2-4 hours in a solvent at the temperature of -20 DEG C to -1 DEG C; and carrying out aftertreatment on reaction liquid so as to obtain a hydroxyhalogenation product; and (3) reacting the hydroxyhalogenation product with an aluminium hydrogenation reagent for 3-8 hours in the solvent at the temperature of 20-70 DEG C, wherein the molar ratio of the aluminium hydrogenation reagent to the hydroxyhalogenation product is (2-6): 1, and carrying out aftertreatment on reaction liquid, thus obtaining the 25-hydroxycholesterol. The synthetic method of the 25-hydroxycholesterol has the characteristics of simple process, environmental protection, few side reactions and high yield.

Description

Technical field [0001] The invention relates to a method for preparing 25-hydroxy cholesterol from 24-dehydrocholesterol, and belongs to a method for preparing 25-hydroxy cholesterol based on hydroxyhalogenation and reductive dehalogenation. Background technique [0002] Vitamin D 3 It belongs to steroid derivatives and is of great significance for bone formation. It can promote the absorption of calcium and phosphorus in the intestines, ensure the content of these two elements in body fluids, and promote the normal calcification of bones. The human body lacks vitamin D 3 Rickets may occur in children, and osteomalacia may occur in adults. Vitamin D 3 The anti-rickets effect is mainly through 1,25-(OH) 2 D 3 To achieve, its biological activity strength is vitamin D 3 10,000 times. After a series of studies, it was found that the 25-position hydroxyl group is vitamin D 3 Common features of metabolites, therefore, as synthetic 1,25-(OH) 2 D 3 The synthesis of 25-hydroxycholestero...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00
Inventor 陈新志赵倩计立钱国平刘建刚王子强
Owner ZHEJIANG UNIV
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