SYNTHESIS OF ANTIGENIC DETERMINANTS FOR YEAST D-MANNANS AND A LINEAR (1-]6)-ALPHA-D-GLUCO-D-MANNAN, AND THEIR PROTEIN CONJUGATES

2-O-Benzoyl-3,4,6-tri-O-benzyl-1-O-tosyl-d-mannopyranose and 2,3,4-tri-O- benzyl-6-O-(N-phenylcarbamoyl)-1-O-tosyl-d-glucopyranose were allowed to react with partially blocked 2-[4-(p-toluenesulfonamido)phenyl]ethyl α-d-manno- and -gluco-pyranosides. Disaccharides having α-d-Manp-(1→2)-α-D-Manp, α-d-manp-(1→6)-α-d-Manp, α-d-Manp-(1→6)-α-d-Manp, and α-d-Glcp-(1→6)-α-d-Manp structures, and a branched trisaccharide having the structure α-d-Manp-(1→2)-[α-d-Manp-(1→6)]-α-d-Manp were synthesized. The oligosaccharides were deblocked with sodium in liquid ammonia to give glycopyranosides having a free primary aromatic amine which were converted into isothiocyanate derivatives with thiophosgene. The functionalized oligosaccharides were then coupled to bovine serum albumin to give protein conjugates. © 1979.