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Indium mediated allylation in carbohydrate chemistry: A convenient synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-arabino-2-heptulose (kamusol)

Indiumunterstützte Allylierung in der Kohlenhydratchemie: Eine einfache Synthese von 3-Desoxy-D-arabino-2-heptulosonsäure (DAH) und 3-Desoxy-D-arabino-2-heptulose (Kamusol)

  • Organische Chemie Und Biochemie
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Summary

A short and economical synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (4) and 3-deoxy-D-arabino-2-heptulose (kamusol,8) has been developed. In the key step of the reaction sequence, the indium mediated allylation ofD-erythrose in an aqueous solvent system was utilized generating a seven carbon backbone which was further transformed into the title compounds.

Zusammenfassung

Eine kurzer und ökonomischer Syntheseweg für 3-Desoxy-D-arabino-2-heptulosonsäure (4) und 3-Desoxy-D-arabino-2-heptulose (Kamusol,8) wurde entwickelt. Im Schlüsselschritt der Synthesesequenz wurde die indiumunterstützte Allylierung vonD-Erythrose in wäßrigen Reaktionsmedien angewendet. Das mittels dieser Methode auf sieben Kohlenstoffatome verlängerte Kohlenhydrat-Grundgerüst konnte einfach in die Titelverbindungen übergeführt werden.

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Authors and Affiliations

  1. Institut für Organische Chemie, Universität Wien, A-1090, Wien, Austria

    R. H. Prenner & W. Schmid

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  1. R. H. Prenner
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  2. W. Schmid
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Prenner, R.H., Schmid, W. Indium mediated allylation in carbohydrate chemistry: A convenient synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-arabino-2-heptulose (kamusol). Monatsh Chem 127, 1045–1050 (1996). https://doi.org/10.1007/BF00807577

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  • DOI: https://doi.org/10.1007/BF00807577

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