Method for synthesizing cholesterol by using pregnenolone as raw material

A technology of pregnenolone and cholesterol, applied in the direction of steroids, organic chemistry, etc., can solve the problems of large consumption of raw and auxiliary materials, uneconomical, heavy pollution, etc., and achieve the effect of low production cost, less raw and auxiliary materials, and environmentally friendly processes

Inactive Publication Date: 2016-01-06
HUNAN KEREY BIOTECH
View PDF2 Cites 18 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This prior art uses turmeric extract saponin as a raw material, and obtains cholesterol (compound 01) through 6 steps of reaction...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing cholesterol by using pregnenolone as raw material
  • Method for synthesizing cholesterol by using pregnenolone as raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of compound (03)

[0035] Add pyridine 500mL, pregnenolone (02) 100g, benzenesulfonyl chloride 61g to a 1000mL reaction flask, stir and react at room temperature for 24 hours, then pour the reaction solution into a large amount of ice water, a large amount of solid is precipitated, filter, and filter the cake with clean water Wash and dry to obtain the intermediate sulfonate wet product. Dissolve the wet product of the sulfonate in 1000 mL of methanol, add 93 g of potassium acetate, heat the reaction mixture to reflux, react under reflux for 2 hours, stop heating and reflux; concentrate under reduced pressure to about 200 mL of methanol, freeze and crystallize to obtain the compound ( 03) 96.00g, molar yield 91.93%;

Embodiment 2

[0036] The synthesis of embodiment 2 compound (03)

[0037] The synthetic method is the same as in Example 1, except that in this example, the consumption of benzenesulfonyl chloride and potassium acetate in Example 1 is adjusted to 67g and 124g respectively.

[0038] 96.36 g of compound (03) was obtained, and the molar yield was 92.27%.

Embodiment 3

[0039] The synthesis of embodiment 3 compound (03)

[0040] The synthetic method is the same as in Example 1, except that in this example, the consumption of benzenesulfonyl chloride and potassium acetate in Example 1 is adjusted to 73g and 155g respectively.

[0041] 95.72 g of compound (03) was obtained, and the molar yield was 91.66%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides a method for synthesizing cholesterol by using pregnenolone as a raw material. The method comprises the following steps: 1) adding potassium acetate into methyl alcohol, and performing a reaction on sulfonate to obtain 6-methoxyl-3,5-cyclo-5alpha-pregn-20-one; 2) performing a reaction on triphenylphosphine and 1-chloro-4-methylpentane in an aprotic solvent to obtain a 4-methylbutyltriphenyl phosphonium chloride solution; 3) adding potassium tert-butoxide into the 4-methylbutyltriphenyl phosphonium chloride solution, and performing a wittig reaction; 4) under the catalysis of a rhodium catalyst, performing an asymmetric hydrogenation reaction to obtain 6-methoxyl-3,5-cyclo-5alpha-cholestane; 5) performing a catalytic hydrolysis deprotection reaction by using sulfuric acid to obtain the cholesterol. The method provided by the invention has the advantages that six-step reactions in the conventional method are simplified into four-step reactions, and a ring-opening reaction in which a great number of hydrochloric acid and a large number of zinc powder are consumed in a route of using saponin as an initial raw material. The synthesizing method is simple in process, the consumption of the raw material and auxiliary materials is low, and the mole yield is high; the method is economical and environmentally friendly, and facilitates industrial implementation.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for synthesizing steroid compounds. Background technique [0002] Cholesterol, also known as cholesterol, is a derivative of cyclopentane polyhydrophenanthrene. As early as the 18th century, people had discovered cholesterol from gallstones. In 1816, chemists named this lipid-like substance cholesterol. Cholesterol is widely present in animals, especially in brain and nerve tissue, and is also high in kidney, spleen, skin, liver and bile. Cholesterol is an indispensable and important substance in animal tissue cells. It not only participates in the formation of cell membranes, but also is a raw material for the synthesis of bile acids, vitamin D and steroid hormones. [0003] At present, cholesterol is mainly extracted from the brains and spines of pigs, cattle, sheep and other animals. Due to the emergence of mad cow disease and Streptococcus suis infectio...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07J9/00
Inventor 左前进甘红星谢来宾
Owner HUNAN KEREY BIOTECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap