The approach to the synthesis of novel amino-C-glycosides

Abstract

Stereoselective 1,3-dipolar cycloadditions of exo-glycals 1 to nitrones 2, 5 and 8 were investigated under the catalysis of Lewis acid or in a refluxing benzene or toluene solution, and afforded the corresponding cycloadducts of ketosyl spiro-isoxazolidines. The reductive cleavage of the N-O bond in the isoxazolidine ring and debenzylation by the catalytic hydrogenation [Pd(OH)₂/C] were approached using the glucose-type cycloadducts 6b and 6e to alkyl-C-glycoside derivatives 12, providing a new access to a novel alkyl-C-glycoside containing an amino group on the side alkyl chain.

Keywords

exo-glycal, C-glycoside, 1,3-dipolar cycloaddition, ketosyl spiro-isoxazolidine