A method for synthesizing cholesterol by using stigmasterol degradation product as raw material

Abstract

The invention provides a method for synthesizing cholesterol by using stigmasterol degradation products as raw materials. The method comprises the following steps: 1) performing an etherification reaction on 3-carbonyl-4-pregnene-22-aldehyde and triethyl orthoformate to obtain 3-ethyoxyl-3,5-pregnadiene-22-aldehyde; 2) preparing a 3-methylbutyltriphenyl phosphonium chloride solution; 3) adding potassium tert-butoxide into the 3-methylbutyltriphenyl phosphonium chloride solution, performing a wittig reaction on the 3-methylbutyltriphenyl phosphonium chloride solution and the 3-ethyoxyl-3,5-pregnadiene-22-aldehyde to obtain 3-ethyoxyl-3,5,22-triene cholestane; 4) catalyzing the 3-ethyoxyl-3,5,22-triene cholestane to perform a selective hydrogenation reaction to obtain 3-ethyoxyl-5-ene cholestane; 5) performing a reaction on the 3-ethyoxyl-5-ene cholestane and acetic anhydride to obtain 3-acetyl-5-ene cholestane; 6) performing a hydrolysis reaction on the 3-acetyl-5-ene cholestane to obtain the cholesterol. The synthesizing method is simple in process, and the mole yield of the cholesterol exceeds 85 percent by using the stigmasterol degradation products which are cheap and easily obtained as the raw materials; the production cost is low, the process is environmentally friendly, and 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] Steroid drugs are a class of drugs that are widely used. The structure of this class of drugs is extremely complex, and it is unfeasible to rely entirely on synthetic methods. It is more feasible to modify the structure of natural products with steroidal skeleton structure. [0003] Cholesterol, also known as cholesterol, is a cyclopentane polyhydrophenanthrene steroid drug. 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. Cholesterol can be extracted from the brains and spines of pigs, cattle, sheep and other animals, but due to the emergence of mad cow disease and Streptococcus suis infection, people have doub...

AI Technical Summary

Problems solved by technology

Stigmasterol can be degraded by microorganisms (such as Nocardia) to obtain degradation products with a steroidal skeleton structure, and the pathway for synthesizing cholesterol with stigmasterol degradation products as starting materials has not been proposed yet

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