Journal
ORGANIC LETTERS
Volume 19, Issue 17, Pages 4596-4599Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02198
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Funding
- Poland's National Science Centre [UMO-2015/19/N/STS/00819]
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A high-yielding, one-pot simultaneous synthesis and full characterization of two regioisomeric C-2-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, similar to 1:1 ratio of 3a vs 3b) is attributed to favorable steric constraints and to a templation by a chloride anion. H-1 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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