Stereocontrolled synthesis of enantiomerically pure unsaturated analogues of 2,6-DAP. Part 5 |
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| Institution: | 1. State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Haihe Education Park, 38 Tongyan Road, Tianjin 300353, People''s Republic of China;2. Structural Biology Laboratory, Tsinghua University, Beijing 100084, People''s Republic of China;1. College of Life Science and Bio-engineering, Beijing University of Technology, 100 Pingleyuan, Chaoyang, Beijing, 100124, PR China;2. International Academy of Targeted Therapeutics and Innovation, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing, 402160, PR China;1. Discovery Chemistry, Merck Research Laboratories, 2000 Galloping Hill Rd., Kenilworth, NJ 07033, USA;2. Drug Metabolism, Merck Research Laboratories, 2000 Galloping Hill Rd., Kenilworth, NJ 07033, USA;3. Discovery Biology, Merck Research Laboratories, 2000 Galloping Hill Rd., Kenilworth, NJ 07033, USA;1. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 02660 Kiev, Ukraine |
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| Abstract: | An efficient new stereocontrolled synthesis of (2R,6R)-(+)- and (2S,6S)-(−)-2,6-diamino-4-methylene-1,7-heptanedioic acid 8a and 9a, respectively, has been accomplished starting from the glycine-derived chiral synthon 1. The enantiomerically pure α-alkyl derivatives 8b–d and 9b–d have also been synthesized. The absolute configuration of the new stereocenters was assigned on the basis of 1H NMR spectra. |
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