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  • Cis- and trans-3-Azido-Oxetan-2-Carboxylate Scaffolds: Hexamers of Oxetane cis-b-Amino Acids.

    Author(s)
    Barker, Sarah F.
    Angus, Donald
    Taillefumier, Claude
    Probert, Michael R.
    Watkin, David J.
    Watterson, Mark P.
    Claridge, Timothy D. W.
    Hungerford, Natasha Lynn
    Fleet, George W. J.
    Griffith University Author(s)
    Hungerford, Natasha L.
    Year published
    2001
    Metadata
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    Abstract
    Efficient synthesis of both cis- and trans-3-azido-oxetane-2-carboxylates relies upon efficient nucleophilic displacements of 3-O-triflates of oxetanes by trifluoroacetate and azide. Such structures are scaffolds for incorporation of oxetane-β-amino acids into oligomers; the synthesis of a series of protected β-hexapeptides and the X-ray crystal structure of methyl 2,4-anhydro-6-deoxy-5-O-benzyl-l-altronate are reported.Efficient synthesis of both cis- and trans-3-azido-oxetane-2-carboxylates relies upon efficient nucleophilic displacements of 3-O-triflates of oxetanes by trifluoroacetate and azide. Such structures are scaffolds for incorporation of oxetane-β-amino acids into oligomers; the synthesis of a series of protected β-hexapeptides and the X-ray crystal structure of methyl 2,4-anhydro-6-deoxy-5-O-benzyl-l-altronate are reported.
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    Journal Title
    Tetrahedron Letters
    Volume
    42
    DOI
    https://doi.org/10.1016/S0040-4039(01)00660-8
    Subject
    Organic Chemical Synthesis
    Medicinal and Biomolecular Chemistry
    Organic Chemistry
    Publication URI
    http://hdl.handle.net/10072/58345
    Collection
    • Journal articles

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