Biological preparing method of key chiral intermediate of levonorgestrel

A technology for a chiral intermediate, levonorgestrel, is applied in the field of preparing a key chiral intermediate of levonorgestrel, can solve the problems of catalyst pollution, unsatisfactory stereoselectivity and the like, and achieves high substrate concentration, high Good stereoselectivity
CN107881202AActive Publication Date: 2018-04-06ZHEJIANG UNIV OF TECH
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
ZHEJIANG UNIV OF TECH
Publication Date
2018-04-06

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Abstract

The invention discloses a biological preparing method of a key chiral intermediate of levonorgestrel. The method includes the steps that wet cells obtained by fermenting cultivation of cryytococcus neoformans ZJPH1704 is used as an enzyme source, an ethyl condensation compound is used as a substrate, phosphate buffer with the pH of 5.8-8.0 is used as a reaction medium, a reaction system is formed,reaction is conducted at the temperature of 30-40 DEG C and the rotating speed of 150-250 rpm, and after the reaction is completed, reaction liquid is separated and purified to obtain the key chiralintermediate of levonorgestrel. The cryytococcus neoformans ZJPH1704 strain is used for catalytic reduction to prepare the intermediate, the key chiral intermediate has the advantages that the catalytic reduction substrate is high in concentration, and the stereoselectivity is high. When the substrate concentration is 7.0 g / L (22.4 mM), the yield reaches 73%, and the ee value is 100%.
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Description

(1) Technical field

[0001] The invention relates to a method for preparing a key chiral intermediate of levonorgestrel by biological reduction of Geotrichum candidum ZJPH1704 strain. (2) Background technology

[0002] Ethyl condensate (chemical name: 2-[2-(3,4-dihydro-6-methoxy-1(2H)-naphthylidene)ethyl]-2-ethylcyclopentane-1, 3-Diketone, CAS No.: 850-92-0) structural formula:

[0003]

[0004] Ethyl Hydroxide (chemical name: 2-ethyl-3-hydroxy-2-[2-(6-methoxy-3,4-dihydro-1(2H)-naphthalene) ethyl]cyclopenta Ketone, CAS number: 51773-49-0) structural formula:

[0005]

[0006] Ethyl hydroxylate is used in the synthesis of progesterone drug levonorgestrel (chemical name: D(-)-17α-ethynyl-17β-hydroxy-18-methylestr-4-en-3-one) The key chiral intermediate of the drug, the drug mainly acts on the hypothalamus and pituitary gland, has good progesterone activity, and a strong ability to bind to androgen receptors. Used in combination with estrogen, it can be used as short-a...

Claims

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