Glycosylation with N-acetyl glycosamine donors using catalytic iron(III) triflate: from microwave batch chemistry to a scalable continuous-flow process

    • Amandine Xolina
    • Arnaud Stévenina
    • Mathieu Pucheaultb
    • Stéphanie Norsikiana
    • François-Didier Boyer*ac
    • Jean-Marie Beau*ad
    • aCentre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Gif-sur-Yvette, France
    • bInstitut des Sciences Moléculaires, CNRS-Université de Bordeaux, Talence, France
    • cInstitut Jean-Pierre Bourgin, UMR1318 INRA-AgroParisTech, Versailles, France
    • dUniversité Paris-Sud and CNRS, Laboratoire de Synthèse de Biomolécules, Institut de Chimie Moléculaire et des Matériaux, Orsay, France

    Efficient and highly selective glycosylation reactions of peracetylated β-D-N-acetyl gluco- and galactosamine are described using catalytic iron(III) triflate under microwave conditions or in a continuous flow process. Simple β-glycosides and β-(1 → 6), β-(1 → 2) and β-(1 → 3) linked disaccharides bearing various protecting groups were obtained in high yields. Insights into the glycosylation mechanism are discussed.

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