稀有糖的氟导向1,2-反式糖基化反应
Fluorine-directed 1,2-trans glycosylation of rare sugars.
作者信息
Aiguabella Nuria, Holland Mareike C, Gilmour Ryan
机构信息
Institute for Organic Chemistry and Excellence Cluster EXC 1003 "Cells in Motion", Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.
出版信息
Org Biomol Chem. 2016 Jun 28;14(24):5534-8. doi: 10.1039/c6ob00025h. Epub 2016 Feb 16.
To reconcile the urgent need to access well defined β-configured 2,6-di-deoxypyranose analogues for chemical biology, with the intrinsic α-selectivity of the native system, the directing role of fluorine at C2 has been explored. Localised partial charge inversion (C-H(δ+)→ C-F(δ-)) elicits a reversal of the substrate-based α-stereoselectivity, irrespective of the protecting group electronics.
为了协调化学生物学中对获取结构明确的β构型2,6-二脱氧吡喃糖类似物的迫切需求与天然系统固有的α选择性，人们对C2位氟原子的导向作用进行了探索。局部部分电荷反转（C-H(δ+)→C-F(δ-)）引发了基于底物的α立体选择性反转，而与保护基的电子效应无关。
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