Synthetic Studies on Selectin Ligands/Inhibitors: One-Pot Synthesis of the Mono- and Oligo-Sulfated 2-(Tetradecyl)Hexadecyl β-D-Galacto- and Lactopyranosides as the Sulfatide Mimetics

Regioselective sulfation through the dibutylstannylene acetals was applied to the key step to prepare a number of sulfated saccharides which are active as the inhibitors of L- and P-selectin. The number and the positions of the sulfate groups were confirmed by NMR and MS analyses. Using this methodology, our target sulfated glycolipids (6-9, 12-14) were conveniently synthesized in one-pot from free 2-(tetradecyl)hexadecyl β-D-galactopyranoside 5 and lactoside 11. 1. Synthetic studies on sialoglycoconjugates, Part 97. For Part 96, see E. Tanahashi, K. Murase, M. Shibuya, Y. Igarashi, H. Ishida, A. Hasegawa and M. Kiso, J. Carbohydr. Chem., previous paper this issue.