The 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: 2015-09-23
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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  • The synthetic method of 25-hydroxycholesterol
  • The synthetic method of 25-hydroxycholesterol
  • The 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, carries out following steps successively:

[0047] 1) With 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 add 10g (about 0.097mmol) dropwise at room temperature ) acetic anhydride (dropped in about 30 minutes). The reaction process was monitored by TLC. After the dropwise addition, the reaction was continued at room temperature for 10 h, and the reaction ended.

[0048] The reaction solution was washed with water (the amount of water used was 50ml×2), pickled (the amount used was 50ml×2 with dilute hydrochloric acid solution with a volume concentration of 5%), and extracted with dichloromethane (the amount used was 30ml×3). Wash with saturated sodium bicarbonate solution until neutral, dry over anhydrous sodium sulfate (about 5 g) and remove the solvent (ie, dichloromethane) to obtain 19.1 g of a...

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 embodiment 1, the difference lies in:

[0058] 1) With 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 drop 10g (about 0.097mmol) of vinegar at room temperature anhydride. The reaction process was monitored by TLC. After the dropwise addition, the reaction was continued at room temperature for 10 h, and the reaction ended.

[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 dried with anhydrous sodium sulfate (about 5g) , and reduced pressure (0.1 MPa) to remove the solvent (ie dichloromethane) by rotary evaporation to obtain 19.0 g of acetylated 24-dehydrocholesterol with ...

Embodiment 3

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

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

[0064] 1) With 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 drop 14.1g (about 0.1mol) of triethylamine at room temperature ) Benzoyl chloride, after the dropwise addition, the temperature was raised to reflux, and the reaction was terminated after 24 hours of reaction.

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

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

[0067] The rest are basically the same as step 2 of Example 1); 0.27g of epo...

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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 reactions. Background technique [0002] Vitamin D 3 Refers to a class of sterol substances that have an important impact on calcium and phosphorus metabolism and bone growth in children. Clinically, it is the main drug for the treatment of rickets, rickets, and hypothyroidism. At present, people through the various vitamin D 3 The study of metabolites not only further clarified the vitamin D 3 Mode of action, also enriched with vitamin D 3 chemical connotation. as vitamin D 3 One of the metabolites of 1,25-(OH) 2 D. 3 The bioactive strength of vitamin D 3 10000 times. But because vitamin D 3 The content of various metabolites of vitamin D in the body is extremely small, and it is very difficult to separate and purify. Therefore, in...

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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