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Communication | Special issue | Vol 86, No. 2, 2012, pp.919-925
Published online, 29th August, 2012
DOI: 10.3987/COM-12-S(N)66
SCANDIUM TRIFLATE-CATALYZED D-FRUCTOFURANOSYLATION REACTIONS USING DISACCHARIDE UNITS

Takashi Yamanoi,* Noriko Misawa, Sho Matsuda, Mikio Watanabe, and Yoshiki Oda

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

Abstract

This paper describes efficient D-fructofuranosylation reactions catalyzed by scandium triflate. The reactions used several benzoylated or benzylated glycosyl acylate derivatives from disaccharides containing the D-fructofuranose moiety at the reducing ends. Only 5 - 10 mol% scandium triflate effectively promoted the D-fructofuranosylation reactions using the disaccharide derivatives as the glycosyl donors. The structures and protecting groups of the disaccharide donors and alcohol acceptor species influenced the stereoselectivity and reactivity of the fructofuranosylation reactions. The fructofuranosylation reactions could be applied to synthesize several non-reducing trisaccharides containing a sucrose-like disaccharide unit.