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Syntheses of model oligosaccharides of biological significance 9. syntheses of trideuteriomethyldi 3 6 o 2 acetamido 2 deoxy beta d glucopyranosyl beta d galactopyranoside the i antigen branch point trisaccharide and related disaccharides



Syntheses of model oligosaccharides of biological significance 9. syntheses of trideuteriomethyldi 3 6 o 2 acetamido 2 deoxy beta d glucopyranosyl beta d galactopyranoside the i antigen branch point trisaccharide and related disaccharides



Canadian Journal of Chemistry 65(4): 693-703



The title trisaccharide, 13c, was synthesized, as well as its two component disaccharides, 10c and 11c. Four disaccharides, 3c, 4c, 5c, and 7c, were also prepared to serve as model compounds for the investigation of the 3-dimensional strucutre of more complex oligosaccharides. The .beta.-1,3 linkage was formed in 75% yield by coupling 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-.beta.-D-glucopyranosyl bromide (9) with trideuteriomethyl 2-O-benzoyl-4,6-benzylidene-.beta.-D-galactopyranoside (2a), using silver trifluoromethanesulphonate as a promoter in the presence of the base 2,5-di-tert-butyl-4-methylpyridine. Using a silver zeolite as a promoter under 9 and silver zeolite with either trideuteriomethyl 2,3-di-O-benzoyl-.beta.-D-galactopyranoside (8b) or trideuteriomethyl 2-O-benzoyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-.beta.-D-glucopyranosyl)-.beta.-D-galactopyranoside (11 b). 2,3,4-Tri-O-benzyl-.alpha.-L-fucopyranosyl bromide (1b) was used in the halide ion catalyzed fucosylation of 2a or its 3-O-benzoyl isomer 2b. The glycosylations of 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-galactopyranosyl)-2-deoxy-2-phthalimido-.beta.-D-glucopyranosyl bromide (6b) and 4-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-galactopyranosyl)-2,3,6-tri-O-acetyl-.alpha.-D-glucopyranosyl bromide (5a) by heptadeuterioisopropanol used silver zeolite as promoter.

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