Synthesis of three disaccharides for the preparation of immunogens bearing immunodeterminants known to occur on glycoproteins
✍ Scribed by Göran Ekborg; Yoshiaki Sone; Cornelis P.J. Glaudemans
- Book ID
- 102991002
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- English
- Weight
- 989 KB
- Volume
- 110
- Category
- Article
- ISSN
- 0008-6215
No coin nor oath required. For personal study only.
✦ Synopsis
p-Nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside was condensed with 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl bromide, the product deprotected, and the disaccharide glycoside converted into p-trifluoroacetamidophenyl 2-acetamido-2-deoxy-4-O-beta-D-galactopyranosyl-beta- D-glucopyranoside. p-Nitrophenyl 3-O-benzoyl-4,6-di-O-benzylidene-alpha-D-mannopyranoside was condensed with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl bromide, and the product was deprotected, to yield p-nitrophenyl 2-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-alpha-D-mannopyranoside. p-Nitrophenyl 2-acetamido-3,4-di-O-benzoyl-2-deoxy-beta-D-glucopyranoside was condensed with 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl bromide, and, after reduction, trifluoroacetylation, and deprotection, p-trifluoroacetamidophenyl 2-acetamido-2-deoxy-6-O-alpha-L-fucopyranosyl-beta-D-glucopyranoside was obtained.