Synthesis and Biological Evaluation of S ‐Neofucopeptides as E‐ and P‐Selectin Inhibitors

The synthesis of α/β‐ L ‐fucosylated cysteamine, 3‐thiopropionic acid, and 3‐thioacetic acid derivatives as building blocks for the preparation of S ‐neofucopeptides is shown. These compounds were used in the synthesis of new thiofucosides derivatives ( 8 α, 9 α, 9 β, 10 α, 22 α, 22 β, 24 α, 26 α) that show affinity towards E‐ and P‐selectins. They constitute a new series of hydrolytically stable and low‐molecular‐weight mimetics of the natural SLe x tetrasaccharide. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)