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

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Title: Application of Appel reaction to the primary alcohol groups of fructooligosaccharides: Synthesis of 6,6',6''-trihalogenated 1-kestose derivatives
Authors: Tachrim, Zetryana Puteri Browse this author
Nakamura, Tadashi Browse this author →KAKEN DB
Sakihama, Yasuko Browse this author →KAKEN DB
Hashidoko, Yasuyuki Browse this author →KAKEN DB
Hashimoto, Makoto Browse this author →KAKEN DB
Keywords: Appel reaction
nuclear magnetic resonance (NMR)
primary alcohol
regioselective halogenations
1-kestose
fructooligosaccharides
Issue Date: 2018
Publisher: Arkat-USA
Journal Title: Arkivoc
Volume: 2018
Issue: 7
Start Page: 341
End Page: 348
Publisher DOI: 10.24820/ark.5550190.p010.706
Abstract: 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 1- kestose were conveniently isolated. Further deprotection of the per-O-acetylated form resulted in 6-, 6’-, and 6’’-trihalogenated derivatives. The structure elucidation by one- and two-dimensional nuclear magnetic resonance established that halogenations are specific at the 6-, 6’-, and 6’’-position of 1-kestose primary alcohols.
Rights: https://creativecommons.org/licenses/by-nc/4.0/
Type: article
URI: http://hdl.handle.net/2115/74376
Appears in Collections:農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 橋本 誠

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