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

Tachrim, Zetryana Puteri; Wang, Lei; Yoshida, Takuma et al.

ChemistrySelect, 2016, 1(1), 58-63

Permalink : https://hdl.handle.net/2115/64879

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論文情報

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アクセス権
open access
URI
https://hdl.handle.net/2115/64879
タイトル
Comprehensive structural analysis of halogenated sucrose derivatives: Revisiting the reactivity of sucrose primary alcohols
著者
Tachrim, Zetryana Puteri ; Wang, Lei ; Yoshida, Takuma ; Muto, Miho ; Nakamura, Tadashi ; Masuda, Katsuyoshi ; Hashidoko, Yasuyuki ; Hashimoto, Makoto
著者名
Tachrim, Zetryana Puteri
著者名
Wang, Lei
著者名
Yoshida, Takuma
著者名
Muto, Miho
著者名
Nakamura, Tadashi
著者名
Masuda, Katsuyoshi
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
NMR
Primary alcohol
Regioselective halogenations
Sucrose
発行日
2016-01
出版者
Wiley-Blackwell
収録物名
ChemistrySelect
巻(号)
1(1)
ページ
58-63
抄録
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'.
資源タイプ
学術雑誌論文
出版タイプ
Version of Record
PISSN
2365-6549
関連情報 (isIdenticalTo)
出版社版DOI
https://doi.org/10.1002/slct.201500003