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 (8α, 9α, 9β, 10α, 22α, 22β, 24α, 26α) that show affinity towards E- and P-selectins. They constitute a new series of hydrolytically stable and low-molecular-weight mimetics of the natural SLex tetrasaccharide. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)