SYNTHETIC STUDIES ON SELECTIN LIGANDS INHIBITORS - SYNTHESIS AND BIOLOGICAL-ACTIVITY OF THE SULFATED AND PHOSPHORYLATED MULTIVALENT BETA-D-GALACTOPYRANOSIDES CONTAINING FATTY ALKYL RESIDUES/

Ten sulfated and three phosphorylated beta-D-galactopyranoside dimers and one sulfated beta-D-galactopyranoside trimer containing fatty alky l residues in place of ceramide have been synthesized. The coupling of 2,3,4,6-tetra-0-acetyl-alpha-D-galactopyranosyl bromide (2) with bran ched fatty alkyl diols and a triol (1a-1j) using mercury bromide as an activating agent gave the corresponding parent glycolipids (4a-4j) in good yields. Regioselective sulfation of these parent glycolipids thr ough the dibutylstannylene acetals produced the target sulfated glycol ipids, 3-sulfate (5a-5j) while stepwise phosphorylation with dibenzylo xy(diisopropylamino)phosphine gave the phosphorylated glycolipids, 3,4 -bisphosphate (9e, g, i). The synthetic glycolipids were assayed for t heir ability to block the adhesion of HL-60 cells to immobilized P-, L - and E-selectin.