Facile Synthesis of Novel Pentofuranose Analogs of Phospha Sugar Derivatives |
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| Authors: | Mitsuji Yamashita Lakonda Nagaprasada Rao Valluru Krishna Reddy Motoki Maeda Tatsuo Oshikawa Masaki Takahashi |
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| Institution: | Department of Materials Chemistry, Faculty of Engineering , Shizuoka University , Hamamatsu , 432-8561 , Japan |
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| Abstract: | Novel pentofuranose analogs of phospha sugar derivatives were synthesized starting from 1-phenyl-2-phospholene 1-oxide ( 1 ). First, the allylic oxidation of 1-phenyl-2-phospholene 1-oxide ( 1 ) with CrO 3 in Ac 2 O-AcOH or 3-hydroxy-1-phenyl-2-phospholene ( 2 ) with MnO 2 afforded 1-phenyl-4-oxo-2-phospholene 1-oxide ( 3 ). The C-5 alkylation of 3 in the presence of NaH by using benzyl bromide or methyl iodide as electrophiles afforded the target title compounds. |
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| Keywords: | Allylic Oxidation C-5 Alkylation Phenyl-2-phospholene |
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