Synthesis of (2S,3S)-2-benzoyl aminometh-3-hydroxy-butyrate ester series compound by asymmetric yeast cell

Abstract

Synthesis of (2S,3S)-2-benzoyl-aminomethyl-3-hydroxy-butyrate ester series compound by yeast cell asymmetry is carried out by taking baker yeast as raw material and converting to obtain the final product by one-step biological method. It's effective and efficient and has better substrate percent conversion.

Description

technical field [0001] The present invention relates to the bioasymmetric synthesis of (2S, 3S)-2-benzamidomethyl-3-hydroxybutyrate represented by formula (I). The compound of formula (I) prepared by the invention is the key intermediate for industrial production of the compound of formula (II) (abbreviated as 4-AA); the compound of formula (II) can be used in the synthesis of carbapenems and penems Intermediate (see Formula 1). [0002] [0003] Formula 1. Background technique [0004] Azetidinone compound 3R, 4R-3-[(1R)-tert-butyldimethylsiloxyethyl]-4-acetoxy-2-azetidinone (formula (II), referred to as 4-AA) is a key intermediate in the synthesis of new high-efficiency antibiotics carbapenems and penems, such as for the synthesis of carbapenem antibiotics imipenem, meropenem, faropenem and panipene Nan et al. [0005] The compound of formula (II) has 3 chiral centers, so there are 8 stereoisomers, which is very difficult to synthesize. There...

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Problems solved by technology

There have been literature reviews on the synthesis process of (II), but most of the processes have disadvantages such as long synthetic route, low total yield, cumbersome operation, and high cost, thus limiting the industrial production of the compound of formula (II)

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