A stereocontrolled cycloaddition route to b-D-glucopyranosyl (1->4)-linked glycals.

Richard P. C. Cousins, Robin G. Pritchard, Clive M. Raynor, Mark Smith, Richard J. Stoodley

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The facial reactivity of I towards electron-deficient aldehydes can be controlled by Ln(fod)3 catalyst selection, providing the basis of a route to glycals of type II [using Yb(fod)3] or III [using La(fod)3] where R = 4-nitrophenyl, 5-nitrofur-2-yl, or 5-nitrothien-2-yl and R1 = 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside.
    Original languageEnglish
    JournalTetrahedron Letters
    Volume43
    DOIs
    Publication statusPublished - 2002

    Keywords

    • Oligosaccharides Role: SPN (Synthetic preparation), PREP (Preparation) (glycal; prepn. of b-D-glucopyranosyl (1->4)-linked glycals using a Ln(fod)3 catalyzed stereocontrolled cycloaddn. as a key step); Cycloaddition reaction; Cycloaddition reaction catalysts (stereoselective; prepn. of b-D-glucopyranosyl (1->4)-linked glycals using a Ln(fod)3 catalyzed stereocontrolled cycloaddn. as a key step)

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