Enantiospecific synthesis of a glycoside of d-epi-purpurosamine |
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| Affiliation: | 1. State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Department of Chemistry, Nankai University, Tianjin 300071, PR China;2. Tianjin Key Laboratory of Structure and Performance for Functional Molecule, College of Chemistry, Tianjin Normal University, Tianjin 300387, PR China;1. Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan;2. Graduate School of Bioscience and Bioindustry, Tokushima University, Tokushima 770-8513, Japan;3. Faculty of Pharmaceutical Sciences, International University of Health and Welfare, Ohtawara 324-8501, Japan;4. School of Pharmacy, Showa University, Shinagawa 142-8555, Japan;5. Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto 862-0082, Japan;6. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kumming Institute of Botany, Chinese Academy of Sciences, Kumming 650201, China;1. Department of Precision Instrument, Tsinghua University, Beijing 100084, PR China;2. Department of Orthodontics, Beijing Stomatological Hospital, Beijing 100050, PR China;3. College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, PR China;1. Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstraße 6, 38678 Clausthal-Zellerfeld, Germany;2. BASF SE, GVM/C—A030, 67056 Ludwigshafen, Germany;1. Nano-Optoelectronics Research and Technology Laboratory, School of Physics, Universiti Sains Malaysia, 11800 Penang, Malaysia;2. Faculty of Electrical Engineering, Universiti Teknologi MARA, Jalan Permatang Pauh, 13500 Permatang Pauh, Pulau Pinang, Malaysia |
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| Abstract: | 2-Propyl d-epi-purpurosaminide dihydrochloride 14 and its di-N-acetylated derivative 15 were synthesized by an enantiospecific sequence which involves the 2-propyl 6-O-acetyl-3,4-dideoxy-α-d-erythro-hex-3-enopyranosid-2-ulose 2 as the key precursor. The first approach through the saturated diol 4, prepared by reduction of the enone system of 2, was unsuccessful as the C-2 position of 2,6-di-O-sulfonyl derivatives 5 and 6 resisted substitution by azide. Therefore, an alternative sequence starting from the allylic alcohol 3, also derived from 2, was developed. In this case, the 2,6-di-O-tosyl derivative 9 gave the expected 2,6-diazide 10 with additional unwanted rearrangement of the double bond to the 2-propyl 4,6-diazido-2,3,4,6-tetradeoxy-α-d-threo-hex-2-enopyranoside 11 isomer. However, the ditriflate derivative 13, analogous to 9, underwent substitution to afford the diazide 10 in good yield. Upon reduction of the azide functions and saturation of the double bond of 10 by catalytic hydrogenation under acidic conditions, the dihydrochloride salt 14 was obtained as a crystalline product (43% overall yield from 3). |
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