Enantioselective Solid–Liquid Extraction of Native Saccharides with Chiral BINOL-Based Pyridine–Phenol Type Macrocycles,Organic Letters

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Enantioselective Solid–Liquid Extraction of Native Saccharides with Chiral BINOL-Based Pyridine–Phenol Type Macrocycles
Organic Letters ( IF 4.9 ) Pub Date : 2019-08-01 00:00:00 , DOI: 10.1021/acs.orglett.9b01980
Yuki Ohishi ₁ , Mikino Murase ₁ , Hajime Abe ₂ , Masahiko Inouye ₁

Affiliation

A chiral 1,1′-bi-2-naphthol (BINOL)-containing pyridine–acetylene–phenol macrocycle and a pyridine–BINOL alternating macrocycle were developed for enantioselective recognition of saccharides. In solid–liquid extraction of native saccharides, these macrocycles selectively extracted one enantiomer from each of a racemic mixture of d/l-fructose, d/l-glucose, and d/l-mannose into a lipophilic solvent. This is the first example in which native saccharides, especially such important hexoses, were enantioselectively extracted with artificial host molecules.

中文翻译：

基于手性BINOL的吡啶-酚类大环化合物对天然糖的对映体固液萃取

开发了一种手性的含1,1'-联-2-萘酚（BINOL）的吡啶-乙炔-苯酚大环和吡啶-BINOL交替大环用于对映体糖的识别。在固液提取天然糖的过程中，这些大环化合物从d / l-果糖，d / l-葡萄糖和d / l-甘露糖的外消旋混合物的每一种中选择性地提取一种对映异构体到亲脂性溶剂中。这是第一个实例，其中用人工宿主分子对映选择性地提取天然糖，尤其是重要的己糖。

更新日期：2019-08-01

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