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

• Amandine Xolin^a
• Arnaud Stévenin^a
• Mathieu Pucheault^b
• Stéphanie Norsikian^a
• 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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