2-O-Benzylglyceraldehyde: A Synthetic Building Block Available in Both Enantiomeric Forms and Configurationally Stable Owing to Rapid Oligomerization

Authors

  • Prof. Dr. Volker Jäger,

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    1. Institut für Organische Chemie der Universität, Am Hubland, D-8700 Würzburg (FRG)
    • Institut für Organische Chemie der Universität, Am Hubland, D-8700 Würzburg (FRG)
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  • Dipl.-Chem. Volkmar Wehner

    1. Institut für Organische Chemie der Universität, Am Hubland, D-8700 Würzburg (FRG)
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  • This work was supported by the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft, and Bayer AG, Wuppertal-Elberfeld. We thank the state of Bavaria for a Graduiertenförderungsstipendium (V. W.), Dr. C. Hubschwerlen (Hoffmann-La Roche, Basel), Dr. A. Kleemann, and Dr. K. Drauz (Degussa AG, Hanau) for donation of chemicals, and H. Sattler for experimental assistance.

Abstract

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The title compound 1 is a very useful chiral glyceraldehyde derivative offering a broad range of possible applications. Both enantiomers were obtained by a new, simple synthesis from the corresponding tartrates. Monomeric 1 undergoes rapid transformation to a mixture of oligomers, which are configurationally stable at room temperature. The products 2 and 3, which are formed with high enantiomeric purity, are also promising as novel differentiated derivatives of known synthetic building blocks.

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