SYNTHESIS OF 3-O-ARABINOSYLATED (1→6)-β-D-GALACTAN EPITOPES

Abstract

Two tetrameric arabinogalactans, β-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-(1→6)-[α-L-arabinofuranosyl-(1→3)]-D-galactopyranose (14) and α-L-arabinofuranosyl-(1→3)-β-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-(1→6)-D-galactopyranose (25), which are good candidates for CCRC-M7 epitope characterization, were synthesized efficiently using a convergent strategy. Migration of an acceptor acetyl group proved to be an obstacle to synthesis, but regioselective glycosylation or 4-O-benzyl protection of the acceptor circumvented this problem allowing efficient synthesis of the 1→6 linked target compounds.