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    A Facilitated Cyclic Ether Formation and Its Potential Application in Solid-Phase Peptide and Organic Synthesis

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    BorchardtR_CPB_48(2)238.pdf (1.146Mb)
    Issue Date
    2000
    Author
    Shan, Daxian
    Zheng, Ailian
    Ballard, C. Eric
    Wang, Wei
    Borchardt, Ronald T.
    Wang, Binghe
    Publisher
    The Pharmaceutical Society of Japan
    Type
    Article
    Article Version
    Scholarly/refereed, publisher version
    Metadata
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    Abstract
    A "trimethyl lock" system has been known to facilitate lactonization reactions through what has been termed a stereopopulation contorl mechanism. We have found that a similar trimethyl lock system can also facilitate cyclic ether formation with the concomitant release of a carboxylic acid in the presence of anhydrous tetrabutylammonium fluoride. To study this base-mediated trimethyl lock-facilitated cyclic ether formation, we synthesized fifteen model compounds. All model compounds underwent base-mediated cyclic ether formation in high yields at 0°C to room temperature (r.t.) with the concomitant release of the attached carboxylate. Such a system potentially could be used for the development of a two-dimensional linker for solid phase peptide and organic synthesis.
    URI
    http://hdl.handle.net/1808/17746
    DOI
    https://doi.org/10.1248/cpb.48.238
    Collections
    • Pharmaceutical Chemistry Scholarly Works [327]
    Citation
    Shan et al. "A Facilitated Cyclic Ether Formation and Its Potential Application in Solid-Phase Peptide and Organic Synthesis." Chemical and Pharmaceutical Bulletin Vol. 48 (2000) No. 2 P 238-244. http://doi.org/10.1248/cpb.48.238

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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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