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1-kestose (O-β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside) is a potential short chain fructooligosaccharide with an inulin-type skeleton. Halogenation of 1-kestose was conducted via the Appel reaction with the use of carbon tetrahalide (CBr4 or CCl4) and triphenylphosphine, which was then followed by conventional acetylation. The per-O-acetylated form of 6,6’,6’’-trihalogenated derivatives of 1kestose were conveniently isolated. Further deprotection of the per-O-acetylated form resulted in 6-, 6’-, and 6’’-trihalogenated derivatives. The structure elucidation by oneand two-dimensional nuclear magnetic resonance established that halogenations are specific at the 6-, 6’-, and 6’’-position of 1-kestose primary alcohols.

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Application of Appel reaction to the primary alcohol groups of fructooligosaccharides: Synthesis of 6,6â€²,6â€²â€²-trihalogenated 1-kestose derivatives