Synthesis of fine chemicals with high added value from sucrose: Towards sucrose-based macrocycles

Jarosz, Sławomir; Sokołowska, Patrycja; Szyszka, Łukasz

doi:10.1016/j.tetlet.2020.151888

Cited by 9 publications

(2 citation statements)

References 51 publications

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“…For many years, our group is involved in the synthesis of macrocyclic derivatives with sucrose scaffold able to recognize chiral and achiral guests. 30 We have prepared a vast array of chiral receptors based on this disaccharide that could effectively complex ammonium salts, 31 amino acid esters, 32 or simple anions. 33 …”

Section: Introductionmentioning

confidence: 99%

Fluorescent Molecular Cages with Sucrose and Cyclotriveratrylene Units for the Selective Recognition of Choline and Acetylcholine

et al. 2021

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The synthesis of four fluorescent diastereoisomeric molecular cages containing cyclotriveratrylene and sucrose moieties connected via the naphthalene linkers is reported. These diastereoisomers were found to be selective and efficient receptors for acetylcholine and choline. Compound P -5a has a better affinity for choline over acetylcholine, while cage M -5a exhibits a higher association constant for acetylcholine over choline. The highest selectivity value was observed for compound M -5a ( K ACh / K Ch = 3.1). Cages P -5a , P -5b , M -5a , and M -5b were fully characterized by the advanced NMR techniques, and ECD spectroscopy was supported by DFT calculations. The binding constants K a of these receptors were determined by fluorescence titration experiments in acetonitrile.

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Section: Introductionmentioning

confidence: 99%

Fluorescent Molecular Cages with Sucrose and Cyclotriveratrylene Units for the Selective Recognition of Choline and Acetylcholine

et al. 2021

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“…On the other hand, sucrose – the cheapest optically pure molecule – can be successfully used as a chiral building block for macrocyclic receptors [19] . Several sucrose‐based macrocycles were already prepared in our laboratory [20] .…”

Section: Introductionmentioning

confidence: 99%

Chiral Molecular Cages Based on Cyclotriveratrylene and Sucrose Units Connected with p‐Phenylene Linkers

et al. 2021

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Four diastereomeric molecular cages based on cyclotriveratrylene (CTV) and sucrose scaffolds, connected via p‐phenylene linkers, were synthesized in a few steps synthesis. The absolute configuration of these diastereoisomers was determined by advanced NMR and ECD spectroscopies supported by DFT calculations. The X‐Ray crystal structure of P‐4 b cage gave an insight into its unique structure. The binding properties of P‐4 a and M‐4 a cages towards small ammonium guests (1‐methylpyridinium and 1,3‐dimethylimidazolium salts) were investigated.

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Development and Diversification of Sugar Beet in Europe

Muir¹,

Anderson²

2021

Sugar Tech

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Synthesis of fine chemicals with high added value from sucrose: Towards sucrose-based macrocycles

Cited by 9 publications

References 51 publications

Fluorescent Molecular Cages with Sucrose and Cyclotriveratrylene Units for the Selective Recognition of Choline and Acetylcholine

Fluorescent Molecular Cages with Sucrose and Cyclotriveratrylene Units for the Selective Recognition of Choline and Acetylcholine

Chiral Molecular Cages Based on Cyclotriveratrylene and Sucrose Units Connected with p‐Phenylene Linkers

Development and Diversification of Sugar Beet in Europe

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