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Stereoselective Synthesis of 2,3-Unsaturated-aza-O-glycosides via New Diastereoisomeric N-Cbz-imino Glycal-Derived Allyl Epoxides

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    Stereoselective Synthesis of 2,3-Unsaturated-aza-O-glycosides via New Diastereoisomeric N-Cbz-imino Glycal-Derived Allyl Epoxides†
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    Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy
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    Organic Letters

    Cite this: Org. Lett. 2007, 9, 22, 4479–4482
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    https://doi.org/10.1021/ol701836a
    Published September 27, 2007
    Copyright © 2007 American Chemical Society
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    Abstract

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    Diastereoisomeric d,l-N-Cbz-imino glycal-derived allyl epoxides 5 and 6 have been synthesized, and their addition reactions with alcohols examined. The reactions lead to the corresponding 2,3-unsaturated-aza-O-glycosides through a new, completely regioselective 1,4-addition process which proceeds with complete substrate-dependent stereoselectivity.

    Copyright © 2007 American Chemical Society

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    †

     Dedicated to Professor Franco Macchia in the occasion of his 70th anniversary.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    Supporting Information Available

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    Experimental details, spectral and analytical data for all reaction products, and theoretical conformational analysis for 5, 6, and 27−30. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Organic Letters

    Cite this: Org. Lett. 2007, 9, 22, 4479–4482
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol701836a
    Published September 27, 2007
    Copyright © 2007 American Chemical Society
    Request reuse permissions

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