Improved synthesis of the valuable peptidomimetic intermediate 3-azido-4-hydroxy cyclopentanoic acid |
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| Institution: | 1. School of Biological and Chemical Sciences, Queen Mary, University of London, Mile End Road, London E1 4NS, UK;2. School of Chemistry, University of Sydney, NSW 2006, Australia;1. Department of Chemistry and Pharmacy, University of Sassari, Via F. Muroni 23/A, 07100 Sassari, Italy;2. CNR, Neuroscience Institute-Milano, Biometra Institute University of Milan, Milan, Via Vanvitelli 32, 20129 Milano, Italy;3. KemoTech Srl, Building 3, Loc. Piscinamanna, 09010 Pula, CA, Italy;4. PharmaNess Scarl, Building 5, Loc. Piscinamanna, 09010 Pula, CA, Italy;1. Engineering Laboratory of Polylactic Acid-Based Functional Materials of Yunnan, School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming 650500, China;2. State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China;1. Department of Innovative Industrial Technology, Hoseo University, Asan, Chungnam 336-851, Republic of Korea;2. Department of Biobased Materials Science, Kyoto Institute of Technology Matsugasaki, Kyoto 606-8585, Japan;1. Key Laboratory of Interface Science and Engineering in Advanced Materials, Ministry of Education, Taiyuan University of Technology, Taiyuan 030024, China;2. Shanxi Research Center of Advanced Materials Science and Technology, Taiyuan 030024, China;3. Key Laboratory for Organic Electronics & Information Displays, Institute of Advanced Materials, Nanjing University of Posts & Telecommunications, Nanjing 210023, China;4. Department of Physics and Optoelectronics, Taiyuan University of Technology, Taiyuan 030024, China;5. Institute of Molecular Functional Materials, Department of Chemistry and Institute of Advanced Materials, Hong Kong Baptist University, Waterloo Road, Hong Kong, China |
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| Abstract: | An improved synthesis of 3-azido-4-hydroxy cyclopentanoic acid 2 is presented. This molecule is useful as a synthetic scaffold for β-turn mimetics on solid phase, with the selectivity of the turns being dependent on the diastereomer employed. A high diastereoselectivity in the synthesis of this molecule in solution is reported, which may then be attached to the solid phase for the synthesis of peptidomimetic libraries. |
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