Synthesis of lactose-based S-linked sialylmimetics of alpha(2,3)-sialosides.

Abstract

A new approach toward the synthesis of lactose-based S-linked sialylmimetics of a(2,3)-linked sialosides is described. These compounds, represented by the general structure 3, were prepared from methyl ߭d-lactoside in 11 steps. It was found that the choice of protecting group was crucial to allow the efficient introduction of sulfur at the 3-position of the galactose ring.