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Communication | Regular issue | Vol 81, No. 5, 2010, pp.1141-1147
Published online, 23rd March, 2010
DOI: 10.3987/COM-10-11916
L-Fructo- and D-Psicofuranosylation Reactions Catalyzed by Scandium Triflate

Takashi Yamanoi,* Toshiaki Ishiyama, Yoshiki Oda, Sho Matsuda, and Mikio Watanabe

*The Noguchi Institute, 1-8-1, Kaga, Itabashi-ku, Tokyo 173-0003, Japan


This paper describes the formation of L-fructo- and D-psicofuranosidic bonds by the scandium triflate catalyzed glycosidation. The reaction of the benzoylated L-fructofuranosyl acetate with an alcohol in the presence of 5 mol% scandium triflate in toluene at room temperature for 3 h stereoselectively afforded the corresponding α-L-fructofuranoside in good yields. Several α-D-psicofuranosides were predominantly obtained in good yields by the reactions between the benzoylated D-psicofuranosyl acetate and alcohols under similar reaction conditions. This method successfully provided the sucrose mimics composed of D-glucopyranose and L-fructofuranose or D-psicofuranose.