Method for synthesizing cholesterol by using pregnenolone as raw material

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...

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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, the steps are long, the yield is low, the consumption of raw and auxiliary materials is large, the pollution is large, and it is uneconomical

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