The Synthesis and Biological Activity of Novel Spiro-isoxazoline C-Disaccharides Based on 1,3-Dipolar Cycloaddition of exo-Glycals and Sugar Nitrile Oxides.

Abstract A series of novel spiro-isoxazoline C-disaccharides were synthesized by the key step of 1,3-dipolar cycloaddition reactions of exo-glycals and sugar nitrile oxides, and followed by catalytic debenzylation in the presence of Pd(OH)2/C. The cycloaddition reactions were carried out stereoselectively and afforded α-isomers exclusively except in the case of galactose. The biological activities of the novel disaccharides against the glycosidases (α-amylase, α-glucosidase, and β-glucosidase) and HIV and BVDV were evaluated.