Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-α-methylserinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one |
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| Institution: | 1. Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China;2. Dongying Tiandong Pharmaceutical Co., Ltd, No.1236, Nan-er road, Dongying, China;1. Department of Surgery, Loma Linda University School of Medicine, Loma Linda, CA, USA;2. Division of Biochemistry, Loma Linda University School of Medicine, Loma Linda, CA, USA;3. Department of Basic Sciences, Loma Linda University School of Medicine, Loma Linda, CA, USA;4. Department of Surgery, Rady Children''s Hospital, San Diego, CA, USA |
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| Abstract: | We report herein, the novel enzymatic desymmetrization of 2-tert-butoxycarbonylamino-2-methyl-1,3-propanediol 1. This method makes it possible to prepare (S)-N-Boc-N,O-isopropylidene-α-methylserinal 3, which is a chiral building block for the synthesis of a variety of α-substituted alanine derivatives. Moreover, optically active (4R)-methyl-4-2-(thiophen-2-yl)ethyl]oxazolidin-2-one 4, one of the key intermediates in the synthesis of a novel immunosuppressant, has been prepared by this methodology. |
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