Synthesis of C-disaccharides using nitrile oxide cycloaddition chemistry

Abstract

The xylose–mannose and xylose–glucose carbon-linked disaccharides 7 and 9 have been synthesised by a sequence in which the key steps are face selective 1,3-dipolar cycloaddition of xylose nitrile oxide (1) to the glucose-derived alkene (2) and reductive hydrolytic cleavage of the resulting 2-isoxazolines.