Application of the N-hydroxymethyl group to the stereoselective synthesis of (3S,4S)-3-aminodeoxystatine derivatives |
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| Affiliation: | 1. Department of Physics, Periyar University, Salem 636011, Tamil Nadu, India;2. Department of Physics, Selvam Arts and Science College (Autonomous), Namakkal 637003, Tamil Nadu, India;1. College of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 210032, China;2. Laboratory of Regenerative Biology, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, China;1. Department of Chemistry, University of Missouri, Columbia, MO 65211, USA;2. Department of Radiology, University of Missouri, Columbia, MO 65212, USA;3. Department of MU Research Reactor Center, University of Missouri, Columbia, MO 65211, USA;4. Harry S. Truman Memorial Veterans’ Hospital, Columbia, MO, USA;1. Key Laboratory of Radiopharmaceuticals (Beijing Normal University), Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China;2. Department of Nuclear Medicine, Beijing Friendship Hospital of Capital Medical University, Beijing, China |
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| Abstract: | Stereoselective synthesis of two 3-aminodeoxystatine derivatives was achieved. Chiral γ-amino-α,β-unsaturated esters containing an N-aminomethyl group undergo the stereoselective conjugate addition with an internal carbamate or amide nitrogen nucleophile. The diastereoselectivity was about 10:1 by 1H NMR. Thus, the 3-aminodeoxystatine derivatives were prepared from commercially available N-Boc-l-leucine in nine steps in overall yields of 26% and 20% for the benzyl carbamate and the acetamide derivatives, respectively. |
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