Journal
ORGANIC LETTERS
Volume 17, Issue 20, Pages 5068-5071Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02558
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- University of Maryland
- National Science Foundation [CHE-1404911]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1404911] Funding Source: National Science Foundation
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A building block approach to the synthesis of Me4CB[8] and Cy2CB[8] by condensation of glycoluril hexamer 1 with bis(cyclic ethers) 2 is reported. X-ray crystallography demonstrates that the equatorial substitution results in an ellipsoidal cavity. Me4CB [8] and Cy2CB[8] display enhanced aqueous solubility and retain the ability to bind to guests (3-9) typical of unsubstituted CB[8]. The higher inherent solubility of Me4CB [8] allowed it to be used as a solubilizing excipient for insoluble drugs.
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