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Synthesis 1998; 1998(4): 409-412
DOI: 10.1055/s-1998-4487
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Simple Synthesis of Aromatic β-C-Nucleosides via Coupling of Aryl Grignard Reagents with Sugar Fluorides

Masataka Yokoyama* , Hirofumi Toyoshima, Miyuki Shimizu, Jun Mito, Hideo Togo
  • *Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho, Inage-ku, Chiba 263, Japan; Fax + 81(43)2 90 28 74; E-mail: yokoyama@science.s.chiba-u.ac.jp
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Publication Date:
31 December 2000 (online)

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The perbenzylated d-ribofuranosyl fluoride is allowed to react with Grignard reagents of aromatic heterocycles such as thiophene, pyrrole, and indole in THF to afford the corresponding β-C-nucleosides in moderate yields. The present process can be also applied to perbenzylated d-glucopyranosyl fluoride and perbenzylated 2-deoxy-d-ribofuranosyl fluoride as sugar donors.

sugar fluorides - Grignard reagents - C-nucleosides - β-selectivity