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

Tachrim, Zetryana Puteri; Nakamura, Tadashi; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hashimoto, Makoto

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

Tachrim, Zetryana Puteri; Nakamura, Tadashi; Sakihama, Yasuko et al.

Arkivoc, 2018, 2018(7), 341-348

Permalink : https://hdl.handle.net/2115/74376

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アクセス権	open access
URI	https://hdl.handle.net/2115/74376
タイトル	Application of Appel reaction to the primary alcohol groups of fructooligosaccharides: Synthesis of 6,6',6''-trihalogenated 1-kestose derivatives
著者	Tachrim, Zetryana Puteri ; Nakamura, Tadashi ; Sakihama, Yasuko ; Hashidoko, Yasuyuki ; Hashimoto, Makoto
著者名 Tachrim, Zetryana Puteri
e-Rad_Researcher 70271749 著者名 Nakamura, Tadashi
e-Rad_Researcher 10344491 著者名 Sakihama, Yasuko
e-Rad_Researcher 40281795 著者名 Hashidoko, Yasuyuki
e-Rad_Researcher 90292094 著者名 Hashimoto, Makoto
言語	英語
キーワード	Appel reaction
	nuclear magnetic resonance (NMR)
	primary alcohol
	regioselective halogenations
	1-kestose
	fructooligosaccharides
発行日	2018
出版者	Arkat-USA
収録物名	Arkivoc
巻(号)	2018(7)
ページ	341-348
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Version of Record
権利情報	Creative Commons Attribution-NonCommercial 4.0 International
PISSN	1551-7012
EISSN	1551-7004
関連情報 (isIdenticalTo)	出版社版DOI https://doi.org/10.24820/ark.5550190.p010.706