ol7b02198_si_001.pdf (7.54 MB)
Chloride-Templated Macrocyclization and Anion-Binding Properties of C2‑Symmetric Macrocyclic Ureas from Sucrose
journal contribution
posted on 2017-08-21, 19:21 authored by Katarzyna Łęczycka-Wilk, Kajetan Dąbrowa, Piotr Cmoch, Sławomir JaroszA high-yielding,
one-pot simultaneous synthesis and full characterization
of two regioisomeric C2-symmetrical macrocycles 3a and 3b from triphosgene and readily available
hexa-O-benzyl-6,6'-diaminosucrose 1 is
reported. The efficient macrocyclization (90% overall yield, ∼1:1
ratio of 3a vs 3b) is attributed to favorable
steric constraints and to a templation by a chloride anion. 1H NMR titration studies and theoretical predictions revealed that
both receptors show similar affinity for acetate and benzoate anions
and enhanced preference for chloride over H2PO4–.
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chloride anioncharacterizationAnion-Binding PropertiespredictiontriphosgeneChloride-Templated Macrocyclizationreceptors showbenzoate anionsUreaacetatehexaaffinity1 H NMR titration studiessteric constraintsmacrocycles 33 bMacrocyclictemplationSucrosebenzylmacrocyclizationPOvs 3 bregioisomeric C 2Symmetricone-potsynthesispreference
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