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Issue 4, 2016
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Stereoselective synthesis of protected L- and D-dideoxysugars and analogues via Prins cyclisations

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Abstract

A de novo approach for the rapid construction of orthogonally protected L- and D-deoxysugars and analogues is described. A novel and robust silicon-acetal undergoes Prins cyclisations with a series of homoallylic alcohols in high yield and excellent stereocontrol. Modified Tamao–Fleming oxidation of the resulting silyltetrahydropyrans gives direct access to deoxyglycoside analogues and the approach was showcased in the synthesis of protected L-oliose, a component of the anticancer agent aclacinomycin A.

Graphical abstract: Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations

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Publication details

The article was received on 01 Nov 2015, accepted on 08 Jan 2016 and first published on 11 Jan 2016


Article type: Edge Article
DOI: 10.1039/C5SC04144A
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Chem. Sci., 2016,7, 2743-2747
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    Stereoselective synthesis of protected L- and D-dideoxysugars and analogues via Prins cyclisations

    R. J. Beattie, T. W. Hornsby, G. Craig, M. C. Galan and C. L. Willis, Chem. Sci., 2016, 7, 2743
    DOI: 10.1039/C5SC04144A

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