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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)
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Submitter: 橋本 誠
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