FeCl3 center dot 6H(2)O/C: An Efficient and Recyclable Catalyst for the Synthesis of 2,3-Unsaturated O- and S-Glycosides

JOURNAL OF CARBOHYDRATE CHEMISTRY(2014)

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Abstract
A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a handy and eco-friendly immobilized catalyst, FeCl3 center dot 6H(2)O/C. A series of 2,3-unsaturated O-and S-glycosides were obtained for bioassay from corresponding 3,4,6-tri-O-acetyl-D-glucal and D-galactal in good to excellent yields (56%-99%) and high anomeric selectivity (alpha/beta = 7: 1 to > 19: 1). Furthermore, the catalyst was efficient on gram-scale reactions and recyclable for at least three times.
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Key words
FeCl3 center dot 6H(2)O/C,Tri-O-acetyl-D-glycals,2,3-Unsaturated glycosides,Ferrier-rearrangement,Recyclable
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