| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344032 | Tetrahedron: Asymmetry | 2012 | 8 Pages |
Two structurally close tetrasaccharides corresponding to the O-antigens of Escherichia coli O127 and Salmonella enterica O13 have been synthesized using a ‘unichemo’ approach and minimum number of reaction steps. The yields of all glycosylation steps were excellent with a high stereochemical outcome. A common synthetic strategy has been adopted for the simultaneous synthesis of two tetrasaccharides.
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p-Methylphenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-d-galactopyranosideC22H23N3O5S[α]D25=-43 (c 1.2, CHCl3)Source of chirality: d-galactose
p-Methoxyphenyl (3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosideC35H36N6O11[α]D25=+224 (c 1.2, CHCl3)Source of chirality: d-galactose
p-Methoxyphenyl (2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosideC33H34N6O10[α]D25=+179 (c 1.2, CHCl3)Source of chirality: d-galactose
p-Methoxyphenyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-d-galactopyranosyl)-(1→3)-(2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosideC55H56N6O16[α]D25=+147 (c 1.2, CHCl3)Source of chirality: d-galactose
p-Methoxyphenyl (3-O-benzyl-4,6-O-benzylidene-β-d-galactopyranosyl)-(1→3)-(2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosideC53H54N6O15[α]D25=+190 (c 1.2, CHCl3)Source of chirality: d-galactose
p-Methoxyphenyl (2,3,4-tri-O-benzyl-α-l-fucopyranosyl)-(1→2)-(3-O-benzyl-4,6-O-benzylidene-β-d-galactopyranosyl)-(1→3)-(2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosideC80H82N6O19[α]D25=+99 (c 1.2, CHCl3)Source of chirality: d-galactose, l-fucose
p-Methoxyphenyl (3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-d-glucopyranosideC35H36N6O11[α]D25=+250 (c 1.2, CHCl3)Source of chirality: d-glucosamine hydrochloride, d-galactose
p-Methoxyphenyl (2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-d-glucopyranosideC33H34N6O10[α]D25=+248 (c 1.2, CHCl3)Source of chirality: d-glucosamine hydrochloride, d-galactose
p-Methoxyphenyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-d-galactopyranosyl)-(1→3)-(2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-d-glucopyranosideC55H56N6O16[α]D25=+118 (c 1.2, CHCl3)Source of chirality: d-galactose, d-glucosamine hydrochloride
p-Methoxyphenyl (3-O-benzyl-4,6-O-benzylidene-β-d-galactopyranosyl)-(1→3)-(2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-d-glucopyranosideC53H54N6O15[α]D25=+106 (c 1.2, CHCl3)Source of chirality: d-galactose, d-glucosamine hydrochloride
p-Methoxyphenyl (2,3,4-tri-O-benzyl-α-l-fucopyranosyl)-(1→2)-(3-O-benzyl-4,6-O-benzylidene-β-d-galactopyranosyl)-(1→3)-(2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-d-glucopyranosideC80H82N6O19[α]D25=-1 (c 1.2, CHCl3)Source of chirality: d-galactose, d-glucosamine hydrochloride
p-Methoxyphenyl (α-l-fucopyranosyl)-(1→2)-(β-d-galactopyranosyl)-(1→3)-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-acetamido-2-deoxy-α-d-galactopyranosideC35H54N2O21[α]D25=+19 (c 1.2, H2O)Source of chirality: d-galactose, l-fucose
p-Methoxyphenyl (α-l-fucopyranosyl)-(1→2)-(β-d-galactopyranosyl)-(1→3)-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-(1→3)-2-acetamido-2-deoxy-α-d-glucopyranosideC35H54N2O21[α]D25=+6 (c 1.2, H2O)Source of chirality: d-glucosamine hydrochloride, d-galactose, l-fucose
