Regioselective Introduction of 2-Propynyl Groups into the C-2 or C-3 Position of Furanoside Ring

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  • Dai Kubota
    Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University6-16-1 Chitosedai, Setagayaku, Tokyo
  • Oyo Mitsunobu
    Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University6-16-1 Chitosedai, Setagayaku, Tokyo

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Abstract

<jats:title>Abstract</jats:title> <jats:p>The reaction of methyl 2,3-anhydro-α-d-ribofuranoside or methyl 2,3-anhydro-5,6-O-cyclohexylidene-α-d-allofuranoside with 2-propynyl metallic reagents exclusively gave the corresponding 2-C-(2-propynyl)-arabino-pentofuranosides and 2-C-(2-propynyl)-altro-hexofuranosides, respectively. In contrast, the β-anomers were selectively attacked at the position 3 to afford the corresponding 3-C-(2-propynyl)furanosides.</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 26 (6), 517-518, 1997-06-01

    Oxford University Press (OUP)

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