Synthesis of novel nucleosides and stereoselectivity of N-glycosidation

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• 作者：Kyosuke Michigami ; Satoshi Uchida ; Miho Adachi ; Masahiko Hayashi ; ^{mhayashi@kobe-u.ac.jp}
• 关键词：N-Glycosidation ; Pyrimidin-2(1H)-one ; Pyrimidin-2(1H)-thione ; Neighboring group participation
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：14 January, 2013
• 年：2013
• 卷：69
• 期：2
• 页码：595-599
• 全文大小：467 K

文摘

An efficient synthetic route for novel nucleosides has been realized. We report the formation of ¦Á-isomers in spite of neighboring group participation by the benzoyl group at the 2-position in N-glycosidation as well as discuss the stereoselectivity observed. We also found that non-silylated pyrimidin-2(1H)-ones and pyrimidin-2(1H)-thiones having aromatic structures reacted with 1-fluororibose in the presence of a Lewis acid to give the corresponding nucleosides in good to high yield.