Highly efficient diastereoselective biocatalytic acylation of a diastereotopic furanose diol and synthesis of key intermediates for amino derivatized bicyclonucleosides

A.K. Prasad, S. Roy, R. Kumar, N. Kalra, J. Wengel, C.E. Olsen, A.L. Cholli, L.A. Samuelson, J. Kumar, A.C. Watterson, R.A. Gross, V.S. Parmar

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    Abstrakt

    The selectivity of Candida antarctica lipase has been demonstrated and employed in the manipulation of a diastereotopic furanose diol as the key step in the synthesis of a novel bicyclo 3-amino-3-deoxy furanose derivative, which is an important intermediate for the synthesis of bicyclic analogs of AZT. The asymmetrization of the diol has been achieved with preferred formation of a monoacylated product with 100% diastereoselectivity. An efficient synthesis of an intermediate in the synthesis of amino derivatized bicyclonucleosides is also described, two such novel compounds containing cycloamino residues have been prepared.

    OriginalsprogEngelsk
    TidsskriftTetrahedron
    Vol/bind59
    Udgave nummer8
    Sider (fra-til)1333-1338
    ISSN0040-4020
    DOI
    StatusUdgivet - 2003

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    Citationsformater

    Prasad, A. K., Roy, S., Kumar, R., Kalra, N., Wengel, J., Olsen, C. E., Cholli, A. L., Samuelson, L. A., Kumar, J., Watterson, A. C., Gross, R. A., & Parmar, V. S. (2003). Highly efficient diastereoselective biocatalytic acylation of a diastereotopic furanose diol and synthesis of key intermediates for amino derivatized bicyclonucleosides. Tetrahedron, 59(8), 1333-1338. https://doi.org/10.1016/S0040-4020(02)01632-0