Protection of phosphonate function by means of ethoxycarbonyl group. A new method for generation of reactive silyl phosphite intermediates.
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概要
- 論文の詳細を見る
Nucleoside ethoxycarbonylphosphonates were prepared by condensation of appropriately protected nucleosides with ethoxycarbonylphosphonic acid. They were easily converted by treatment with 1 M NaOH followed by trimethylsilylation to highly reactive bis(trimethylsilyl) nucleoside phosphite intermediates which were allowed <I>in situ</I> to react with water, diphenyl disulfide, 2,2′-dipyridyl disulfide, and aldehydes to afford the corresponding nucleoside phosphonates, nucleoside <I>S</I>-phenyl phosphorothioates, nucleoside phosphates, and nucleoside α-hydroxy phosphonates in good yields, respectively. The nucleoside phosphonates were further converted to nucleosides under mild acidic conditions. Thus, the ethoxycarbonyl group proved to serve as a versatile protecting group for not only H–P(O) but also HO–P(O) and hydroxyl groups of sugars.
- 公益社団法人 日本化学会の論文
著者
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Mori Hiroyuki
Department Of Biological Information Graduate School Of Bioscience And Biotechnology Tokyo Institute
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Sekine Mitsuo
Department Of Life Chemistry Tokyo Institute Of Technology
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Hata Tsujiaki
Department of Chemistry Tokyo Institute of Technology
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Mori Hiroyuki
Department of Life Chemistry, Tokyo Institute of Technology
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MORI Hiroyuki
Department of Agricultural Chemistry, Kochi University
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