Synthesis of methyl O-α-l-fucopyranosyl-(1→2)-O-β-d-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-β-d-glucopyranoside, using 2,3,4-tri-O-benzoyl-α-l-fucopyranosyl bromide as the α-l-fucosylating agent
✍ Scribed by Nikolay E. Nifant'ev; Alexander S. Shashkov; Nikolay K. Kochetkov
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- English
- Weight
- 398 KB
- Volume
- 226
- Category
- Article
- ISSN
- 0008-6215
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Condensation of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-a-D-galactopyranoside with 2,3,4-tri-o-acetyl-a-D-fucopyranosyl bromide in 1: 1 nitromethane-benzene, in the presence of powdered mercuric cyanide, afforded benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-0-(2,3,4-tri-O-acetyl-P-D-fucopyran
Treatment of benzyl 2-acetamido-2-deoxy-alpha-D-galactopyranoside with 4-methoxybenzaldehyde dimethyl acetal in N,N-dimethylformamide in the presence of 4-toluenesulfonic acid afforded the 4,6-O-(4-methoxybenzylidene) acetal, which was glycosylated with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosy
Halide-assisted glycosyIation, using a non-p~icipating Z-substituent (benzyl) in the glycosyl halide, was used to obtain the ~-D-gaiactosyl linkage and silver triflate promotion with a participating 2-substituent (benzoyl) was used to obtain the /3-D-galactosyl linkage in a facile synthesis of the t