Synthesis of novel nucleosides and stereoselectivity of N-glycosidation

Synthesis of novel nucleosides and stereoselectivity of N-glycosidation

An efficient synthetic route for novel nucleosides has been realized. We report the formation of α-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 pyrimid...

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Veröffentlicht in:Tetrahedron 2013-01, Vol.69 (2), p.595-599
Hauptverfasser: Michigami, Kyosuke, Uchida, Satoshi, Adachi, Miho, Hayashi, Masahiko
Format: Artikel
Sprache:eng
Schlagworte:
Formations
Lewis acid
N-Glycosidation
Neighboring group participation
Nucleosides
Pyrimidin-2(1H)-one
Pyrimidin-2(1H)-thione
Stereoselectivity
Synthesis
Tetrahedrons
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Zusammenfassung:An efficient synthetic route for novel nucleosides has been realized. We report the formation of α-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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.11.017