Stereoselective synthesis of (2R,3S,4S,5R)-trans-3,4-dihydroxy-5-(4-fluorophenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)tetrahydrofuran and (2R,3S,4S,5R)-trans-5-ethynyl-2-(4-fluorophenoxymethyl)-3,4-O-isopropylidene tetrahydrofuran from mannose diacetonide |
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| Institution: | 1. Key Laboratory of New Energy and Rare Earth Resource Utilization of State Ethnic Affairs Commission, College of Physics and Materials Engineering, Dalian Minzu University, 18 Liaohe West Road, Dalian, 116600, PR China;2. College of New Energy, Bohai University, Jinzhou, 121000, PR China;1. School of Life Science and Biotechnology, Dalian University of Technology, Dalian 116024, China;2. School of Food and Environment Science and Technology, Dalian University of Technology, Panjin 124221, China;3. National Center for Pharmaceutical Screening, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China |
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| Abstract: | Stereoselective synthesis of pharmaceutically interesting chiral tetrahydrofurans starting from mannose diacetonide is reported. A 1,4-diol system derived from mannose diacetonide, through a Mitsunobu reaction was stereospecifically cyclized to give chiral tetrahydrofurans. Both the C-1 and C-4 centers of d-mannose are successfully exploited to install the requisite side chains. |
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