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The total chemical synthesis of the pentasaccharide repeating unit of the O -polysaccharide from E. coli O132 is accomplished in the form of its 2-aminoethyl glycoside. The 2-aminoethyl glycoside is particularly important as it allows further glycoconjugate formation utilizing the terminal amine without affecting the stereochemistry of the reducing end. The target was achieved through a [3 + 2] strategy where the required monosaccharide building blocks are prepared from commercially available sugars through rational protecting group manipulation. The NIS-mediated activation of thioglycosides was used extensively for the glycosylation reactions throughout.

beilstein journal of organic chemistry

Chemical synthesis of the pentasaccharide repeating unit of the <i>O</i>-specific polysaccharide from <i>Escherichia coli</i> O132 in the form of its 2-aminoethyl glycoside

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside