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Palladium(II)-catalyzed intramolecular aminoacetoxylation of sugar derived alkenyl tosylsulfonamide: Total synthesis of l-deoxyallonojirimycin

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Abstract Palladium catalyzed intramolecular aminoacetoxylation of d -ribose derived alkenyl tosylsulfonamide to deliver l -deoxyallonojirimycin in an overall yield of 19%. The preliminary screening of l -deoxyallonojirimycin against carbohydrate processing… Click to show full abstract

Abstract Palladium catalyzed intramolecular aminoacetoxylation of d -ribose derived alkenyl tosylsulfonamide to deliver l -deoxyallonojirimycin in an overall yield of 19%. The preliminary screening of l -deoxyallonojirimycin against carbohydrate processing enzymes showed moderate inhibitory activity against α-glucosidase (yeast) and α-mannosidases.

Keywords: intramolecular aminoacetoxylation; palladium catalyzed; alkenyl tosylsulfonamide; derived alkenyl; catalyzed intramolecular

Journal Title: Tetrahedron Letters
Year Published: 2017

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