Synthesis process of chlesterol and its intermediate

A synthetic method and cholesterol technology, applied in the direction of steroids, organic chemistry, etc., can solve the problems of unsuitability for industrial production and low yield, and achieve the effect of high yield, high yield and simple reaction process

Inactive Publication Date: 2006-05-17
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 1951, R.B Woodward completed the total synthesis of cholesterol. However, the method used by him required more than 30 steps in the reaction pathway, and the yield was very low, which was not suitable for industrial production.

Method used

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  • Synthesis process of chlesterol and its intermediate
  • Synthesis process of chlesterol and its intermediate
  • Synthesis process of chlesterol and its intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment one: the synthetic method of cholesterol, comprises the following steps:

[0040] [Protection of Hydroxyl]: 6.0 grams (0.15mol) of 60% sodium hydride is placed in a 1L three-necked flask, 500ml of anhydrous treated tetrahydrofuran is added, and 41.6 grams (0.1mol) of diosgenin is added in batches under stirring Wherein, after the addition, continue to stir and react for 15 minutes, then add 18.9 grams (0.15mol) of dimethyl sulfate to the mixed solution, stir the reactant at room temperature overnight, add methanol to the reaction system to decompose excess sodium hydride, until the addition No gas was generated from methanol, the mixed solution was poured into 2L of water, cooled and filtered, and the crude product was recrystallized with methanol to obtain 40.6 g of white needle-like crystals. Melting point: 184.5-185.0°C, yield: 95.3%.

[0041] [Ring-opening reaction]: 20 grams (0.046mol) of diosgenin 3-methyl ether and 300 grams (4.6mol) of high-quality z...

Embodiment 2

[0047] Embodiment 2: A kind of synthetic method of cholesterol, take diosgenin as raw material, carry out following treatment:

[0048] (1) Protection of hydroxyl group: in the presence of an organic solvent, treat diosgenin with sodium hydride or potassium hydride to obtain sodium diosgenate or potassium diosgenate, and the reaction molar ratio is 1:1.2-2.0; Then react with dimethyl sulfate, the reaction molar ratio is 1:1.0~2.0, remove excess sodium hydride or potassium hydride with methanol, cool and filter in water, and recrystallize to obtain diosgenin-3-methyl ether;

[0049] (2) Ring-opening reaction: the obtained diosgenin-3-methyl ether is added together with zinc powder in absolute ethanol, the suspension is heated to reflux, concentrated hydrochloric acid is slowly added dropwise, and the reaction product is suction filtered and recrystallized, To obtain 16,26-dihydroxycholesterol-3-methyl ether, the molar ratio of diosgenin-3-methyl ether, hydrochloric acid and zin...

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Abstract

The synthesis process of cholesterol with diosgenin as material includes the following six steps: protecting hydroxyl radical, ring-opening reaction, sulfonylation reaction, reducing sulfonate, methyl ether radical acetylation and saponification to obtain cholesterol. The present invention also discloses two kinds of the intermediate obtained in the process, i. e., 16, 26-dihydroxy cholesterol-3-methyl ether and 16, 26-dimethyl sulfonyl cholesterol-3-methyl ether. The present invention has simple reaction process and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of steroids, in particular to a synthesis method of cholesterol and an intermediate obtained in the synthesis method. Background technique [0002] Cholesterol has a steroidal skeleton and is an important raw material for the synthesis of steroidal compounds. Using Mycobacterium martensii to degrade cholesterol 4-androstane-3,17-dione (4AD) and androstane-1,4-diene-3,17-dione (ADD) into testosterone, Ethinyl testosterone, estradiol, and norethindrone are used to produce sex hormones, fattening hormones, childbirth aids, and oral contraceptives; artificial bezoar ingredients contain 2% cholesterol; cholesterol in pharmaceuticals is used as an emulsifier and an auxiliary agent for pharmaceutical preparations, because it It can increase the emulsification and penetration of medicinal oils in medicaments. It is also a hydrophilic and water-absorbing ointment matrix. It can also be use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
Inventor 朱永明秦烈娜刘蕊
Owner SUZHOU UNIV
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