Abstract
The synthesis is reported of galactopyranose nucleophiles monofluorinated at positions 3, 4, or 6 and protected by 4,6-O-benzylidene, 3,6-di-O-benzyl, or 3,4-O-isopropylidene groups, respectively. The condensation of these nucleophiles with 2,3,4-tri-O-benzoyl-alpha-L-rhamnosyl bromide gave, after deprotection, the disaccharide analogues of methyl O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-D-galactopyranoside, monofluorinated at position 3, 4, or 6 of the galactoside residue.
MeSH terms
-
Carbohydrate Conformation
-
Carbohydrate Sequence
-
Disaccharides / chemical synthesis*
-
Disaccharides / chemistry
-
Fluorides*
-
Fluorine
-
Galactose
-
Indicators and Reagents
-
Ligands
-
Magnetic Resonance Spectroscopy
-
Molecular Sequence Data
-
O Antigens
-
Optical Rotation
-
Polysaccharides, Bacterial / chemistry*
-
Rhamnose
-
Shigella dysenteriae / chemistry*
-
Shigella dysenteriae / immunology
Substances
-
Disaccharides
-
Indicators and Reagents
-
Ligands
-
O Antigens
-
Polysaccharides, Bacterial
-
Fluorine
-
Fluorides
-
Rhamnose
-
Galactose