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, FranceRead the publication that featured this abstract
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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