SYNTHESE EINES N-ACETYLNEURAMINSAEURE-HALTIGEN SYNTHESEBLOCKS. KUPPLUNG ZUM N-ACETYLNEURAMINSAEURE-TETRASACCHARID MIT TRIMETHYLSILYLTRIFLAT

Article abstract of DOI:10.1016/S0008-6215(00)90670-0

A trisaccharide synthetic block consisting of N-acetylneuraminic acid and lactosamine that allows general coupling reactions to other saccharide units was obtained.O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α- and -β-D-glycero-D-galacto-2-nonulopyranosylonate)-(2->6)-O-(2,3,4-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-1,3,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranose were used as glycosyl donors.In the presence of trimethylsilyltriflate, both compounds were converted into tetrasaccharides by reaction with derivatives of D-mannose unsubstituted at OH-2 representing the glycosyl acceptors.Removal of the protecting groups gave O-(5-acetamido-3,5-dideoxy-α- and -β-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-β-D-galactopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-D-mannopyranose, respectively.