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Asymmetric Bioreduction of 3,5-Bis(trifluoromethyl) Acetophenone to Its Corresponding Alcohol by Candida troplcalis 被引量:4

Asymmetric Bioreduction of 3,5-Bis(trifluoromethyl) Acetophenone to Its Corresponding Alcohol by Candida troplcalis
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摘要 (S)-3,5-bistrifluoromethylphenyl ethanol is a key chiral intermediate for the synthesis of NK-1 receptor antagonists. Enantioselective synthesis of (S)-3,5-bistrifluoromethylphenyl ethanol was successfully performed in high enantiomeric excess (e.e.) through asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone catalyzed by Candida tropicalis 104 cells. The influence of some key reaction parameters such as substrate concentration, co-substrate and its concentration, biomass and reaction time was examined, respectively. The results showed that these factors obviously influence the yield, but the optical purity of the prepared product remains intact. The opti-mum conditions for the preparation of (S)-3,5-bistrifluoromethylphenyl ethanol were found to be as follows: sub-strate concentration 50 mmol?L?1; 50 g·L-1 of maltose as co-substrate; wet cell concentration 300 g·L-1; reaction for 30 h. Under above optimal conditions, the maximum yield for (S)-3,5-bistrifluoromethylphenyl ethanol reached 70.3% with 100% of product e.e. (S)-3,5-bistrifluoromethylphenyl ethanol is a key chiral intermediate for the synthesis of NK-1 receptor antagonists. Enantioselective synthesis of (S)-3,5-bistrifluoromethylphenyl ethanol was successfully performed in high enantiomeric excess (e.e.) through asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone catalyzed by Candida tropicalis 104 cells. The influence of some key reaction parameters such as substrate concentration, co-substrate and its concentration, biomass and reaction time was examined, respectively. The results showed that these factors obviously influence the yield, but the optical purity of the prepared product remains intact. The opti-mum conditions for the preparation of (S)-3,5-bistrifluoromethylphenyl ethanol were found to be as follows: sub-strate concentration 50 mmol?L?1; 50 g·L^-1 of maltose as co-substrate; wet cell concentration 300 g·L^-1; reaction for 30 h. Under above optimal conditions, the maximum yield for (S)-3,5-bistrifluoromethylphenyl ethanol reached 70.3% with 100% of product e.e.
出处 《Chinese Journal of Chemical Engineering》 SCIE EI CAS CSCD 2011年第6期1028-1032,共5页 中国化学工程学报(英文版)
基金 Supported by the National'Natural Science Foundation of China (21076193) and Foundation of Zhejiang Key Developing Discipline of Pharmacy (20100609).
关键词 Candida tropicalis asymmetric reduction ENANTIOSELECTIVITY 3 5-bis(trifluoromethyl) acetophenone (S)-3 5-bistrifluoromethylphenyl ethanol 不对称还原反应 热带念珠菌 三氟甲基 苯乙酮 乙醇 不对称合成 底物浓度 细胞浓度
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