An efficient total synthesis of a conjugation-ready trisaccharide
repeating unit of Staphylococcus aureus strain M
is reported here. The main challenges involved in this synthesis are
the procurement of rare sugars (d-FucNAc and d-GalNAcA)
and installation of consecutive 1,2-cis-glycosidic
linkages between them. Stereoselective 1,2-cis glycosylation
with the linker acceptor was achieved with easily accessible benzylidene
protected d-galactosamine thioglycoside by employing a DMF
modulated preactivation glycosylation method. The consecutive 1,2-cis linkages were installed with the help of solvent participation.
The carboxylic acid functionality was introduced via postglycosylation
oxidation on the disaccharide moiety. The total synthesis of trisaccharide
repeating unit was accomplished with the longest linear sequence of
24 steps in 4.5% overall yield.
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