Tetrahedron

Synthesis of novel nucleosides and stereoselectivity of N-glycosidation

K Michigami, S Uchida, M Adachi, M Hayashi

Index: Michigami, Kyosuke; Uchida, Satoshi; Adachi, Miho; Hayashi, Masahiko Tetrahedron, 2013 , vol. 69, # 2 p. 595 - 599

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Citation Number: 4

Abstract

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 ...