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An improved method for the Ferrier sulfonamidoglycosylation of tri-O-acetyl-d-glucal with different N-nucleophiles has been developed. ZnCl 2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 3,4,6-tri-O-acetyl-d-glucal into 2,3-unsaturated-N-pseudoglycals with good yields and preferential α-anomeric selectivity.
A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system. Phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-d-glycal to 2,3-unsaturated O-glycosides. A wide range of alcohols including naturally bioactive compounds could be coupled with the glycal to give the desired products in good to excellent yields and with high...
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