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Comprehensive structural analysis of halogenated sucrose derivatives: Revisiting the reactivity of sucrose primary alcohols

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Title: Comprehensive structural analysis of halogenated sucrose derivatives: Revisiting the reactivity of sucrose primary alcohols
Authors: Tachrim, Zetryana Puteri Browse this author
Wang, Lei Browse this author
Yoshida, Takuma Browse this author
Muto, Miho Browse this author
Nakamura, Tadashi Browse this author
Masuda, Katsuyoshi Browse this author
Hashidoko, Yasuyuki Browse this author
Hashimoto, Makoto Browse this author →KAKEN DB
Keywords: Appel reaction
Primary alcohol
Regioselective halogenations
Issue Date: Jan-2016
Publisher: Wiley-Blackwell
Journal Title: ChemistrySelect
Volume: 1
Issue: 1
Start Page: 58
End Page: 63
Publisher DOI: 10.1002/slct.201500003
Abstract: Regioselective halogenations of sucrose primary alcohols can simplify the synthesis of carbohydrate-based products. The Appel reaction, using carbon tetrahalide (CBr4 or CCl4) and triphenylphosphine, offers efficient conversion of primary hydroxyl groups to halide. Previous halogenation of sucrose with limited amounts of Appel reagent gave obscure result-regarding the halogenation selectivity of sucrose primary alcohols at 6-and 6'-position. Within careful purification of its per-O-acetylated form, re-subjection of sucrose into Appel reaction resulted in two mono-and one dihalogenated products only at 6-and/or 6'-position. Extensive NMR analyses support the revision of previous literature's assignments. Comprehensive analysis of each monohalogenated sucrose at the primary position, including the first reported 1'-monohalogenated sucrose derivatives synthesis via regioselective enzymic deacetylation, provided halogenation of sucrose primary alcohols by the Appel reaction followed the order of 6> 6'>> 1'.
Type: article
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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