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

作者：Tachrim Zetryana Puteri; Wang Lei; Yoshida Takuma; Muto Miho; Nakamura Tadashi; Masuda Katsuyoshi; Hashidoko Yasuyuki; Hashimoto Makoto^*

来源：ChemistrySelect, 2016, 1(1): 58-63.

DOI：10.1002/slct.201500003

• Appel reaction
• NMR
• Primary alcohol
• Regioselective halogenations
• Sucrose

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'.

• 出版日期2016-1