Synthesis of the trisaccharide component of the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae type 19F
Articolo
Data di Pubblicazione:
1987
Citazione:
Synthesis of the trisaccharide component of the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae type 19F / L. Panza, F. Ronchetti, G. Russo, L. Toma. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 0(1987), pp. 2745-2747. [10.1039/p19870002745]
Abstract:
Acetolysis of methyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-mannopyranosyl)-2,3,6-triO-benzyl-α-D-glucopyranoside (3) followed by treatment with hydrogen bromide–acetic acid afforded 4-O-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosyl)-6-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide (5). Compound (5) by Hg(CN)2–HgBr2 promoted condensation with benzyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (6) provided the glycosylation product (22% yield) exclusively in the α-configuration.
Hydrogenolysis of the benzyl protecting groups of the obtained trisaccharide and O-deacetylation of the 6′ and 6″ positions eventually furnished O-(2-acetamido-2-deoxy-β-D-mannopyranosyl)-(1→4)-O-α-D-glucopyranosyl-(1→2)-α,β-L-rhamnopyranose (1), the trisaccharide component of the repeating unit of Streptococcus pneumoniae type 19F.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
L. Panza, F. Ronchetti, G. Russo, L. Toma
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