SYNTHETIC STUDIES ON SELECTIN LIGANDS INHIBITORS - ONE-POT SYNTHESIS OF THE MONO-SULFATED AND OLIGO-SULFATED 2-(TETRADECYL)HEXADECYL BETA-D-GALACTOPYRANOSIDES AND LACTOPYRANOSIDES AS THE SULFATIDE MIMETICS/

Regioselective sulfation through the dibutylstannylene acetals was app lied 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)hexad ecyl beta-D-galactopyranoside 5 and lactoside 11.