Chemical Modification of Lactose. XVII. Syntheses of O-α- and O-β-L-Fucopyranosyl-(1→4)- or -(1→6)-O-β-D-galactopyranosyl-(1→4)-D-glucopyranoses (4'- or 6'-O-α- and -O-β-L-Fucopyranosyllactoses)

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1,6-Anhydro-2,2', 3,3', 6'- and -2,2', 3,3', 4'-penta-O-benzyl-β-lactoses (4 and 7) were synthesized from 1,6-anhydro-2,2', 3,3'-tetra-O-benzyl-4', 6'-O-benzylidene-β-lactose (1). Condensation of 4 with 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide (acetobromofucose) in the conventional Koenigs-Knorr reaction, followed by deacetylation, gave 4'-O-linked trisaccharide derivatives bearing α- and β-L-fucopyranosyl linkages (10 and 15) in 13.4 and 25.6% yields, respectively. Analogous condensation of 7 with acetobromofucose gave a 6'-O-linked, fully protected trisaccharide bearing a β-L-fucopyranosyl linkage (20) in 64% yield. Halide ion-catalyzed condensation of 7 with 2,3,4-tri-O-benzyl-α-L-fucopyranosyl bromide gave a trisaccharide derivative bearing an α-L-fucopyranosyl linkage (26) in 51.8% yield. Removal of the protecting groups of 10,15,20,and 26 provided the title trisaccharides (14,19,25,and 30). ^1H- and ^<13>C-NMR spectral data of 14,19,25,30,and synthetic intermediates are also presented.
公益社団法人日本薬学会の論文
1983-01-25