Synthetic method of 25-hydroxycholesterol

A technology of hydroxycholesterol and synthesis method, applied in the direction of steroids, organic chemistry, etc., can solve the problems of poor selectivity and low yield, and achieve the effects of high selectivity, lower reaction temperature, and higher yield

Active Publication Date: 2014-03-12
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

[0046] Embodiment 1, a kind of synthetic method of 25-hydroxycholesterol, carry out the following steps successively:

[0047] 1) Using 120mL pyridine as solvent and 30mL pyridine (about 0.372mol) as acid binding agent, add 20g of 24-dehydrocholesterol (about 0.052mol) and 0.2g of DMAP, and dropwise add 10g (about 0.097mmol) at room temperature ) acetic anhydride (about 30 minutes to complete). The reaction process was monitored by TLC. After the dropwise addition, the reaction was continued at room temperature for 10 h, and the reaction was completed.

[0048] The reaction solution was washed with water (the amount of water was 50ml×2), and acid washed (with a volume concentration of 5% dilute hydrochloric acid solution, the amount was 50ml×2), and then extracted with dichloromethane (the amount was 30ml×3), and the extract was Washed with saturated sodium bicarbonate solution until neutral, dried with anhydrous sodium sulfate (about 5 g), and then dehydrated the solvent (ie...

Embodiment 2

[0056] Embodiment 2, a kind of synthetic method of 25-hydroxycholesterol,

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

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

[0059] The reaction solution was washed successively with dilute hydrochloric acid (volume concentration 5%, dosage 50ml×2), saturated sodium bicarbonate solution (30ml×2), saturated sodium chloride solution (30ml), and then dried with anhydrous sodium sulfate (about 5g) , and the solvent (ie, dichloromethane) was removed by rotary evaporation under reduced pressure (0.1 MPa) to...

Embodiment 3

[0062] Embodiment 3, a kind of synthetic method of 25-hydroxycholesterol,

[0063] In this embodiment 3, steps 1) and 2) are different from those in embodiment 1, and the difference lies in:

[0064] 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 14.1g (about 0.1mol) at room temperature ) benzoyl chloride, the temperature was raised to reflux after the dropwise addition, and the reaction was terminated after 24 hours of reaction.

[0065] The rest is basically equivalent to step 1) of Example 2, to obtain 23.2 g of benzoylated 24-dehydrocholesterol with a yield of 95.0%.

[0066] 2) Use 40% peracetic acid 0.4g (2mmol) as the epoxidation reagent to replace "38% (mass concentration) peracetic acid 0.4g (2mmol)" in Example 1, and the reaction temperature is changed from -10 ℃ to -20°C.

[0067] The rest are basically equivalent to step 2) of Example 1; 0.2...

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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 as to obtain acylated 24-dehydrocholesterol; (2) carrying out epoxidation reaction on double bonds on the 24th site of the product obtained in the step (1), namely carrying out epoxidation reaction on the acylated 24-dehydrocholesterol and an epoxidation reagent in a solvent II under the catalytic action of manganese salt so as to obtain an epoxidation product; and (3) carrying out reduction ring opening on the epoxidation product obtained in the step (2), namely carrying out reduction ring opening on the epoxidation product obtained in the step (2) and a reduction reagent in a solvent III so as to obtain the 25-hydroxycholesterol. The synthetic method of the 25-hydroxycholesterol has the advantages that peroxyacetic acid and meta-chloroperoxybenzoic acid which are non-toxic and low in cost are used as the epoxidation reagents and environmentally-friendly, the reaction is carried out at a low temperature, and the manganese salt is used as a catalyst and is high in selectivity.

Description

technical field [0001] The invention relates to a method for synthesizing 25-hydroxycholesterol from 24-dehydrocholesterol, in particular to a method for synthesizing 25-hydroxycholesterol based on epoxidation and reduction ring-opening reaction. Background technique [0002] Vitamin D 3 It refers to a class of steroids that have important effects on calcium and phosphorus metabolism and bone growth in children. At present, people through various vitamin D 3 The study of metabolites not only further elucidates vitamin D 3 mode of action, also enriched with vitamin D 3 The meaning of chemistry. as vitamin D 3 One of the metabolites of 1,25-(OH) 2 D 3 The bioactive strength of vitamin D is 3 10,000 times. But because of vitamin D 3 The content of various metabolites in the body is extremely small, and it is very difficult to separate and purify them. Therefore, in order to study their physiological functions, these vitamin D have to be chemically synthesized. 3 meta...

Claims

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Application Information

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Patent Type & Authority Applications(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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