Chemical Synthesis of the Linker‐Armed Trisaccharide Repeating Unit of the O‐Antigen from Pseudomonas putida BIM B‐1100

Abstract

The manuscript reports the concise chemical synthesis of the trisaccharide repeating unit of the O‐antigen from Pseudomonas putida BIM B‐1100 in the form of its aminoethyl glycoside through a linear strategy with rational protecting group manipulations. The challenging aspects of this synthesis include the incorporation of the β‐D‐ManpNAcA and the α‐D‐GlcpNAc residues. The introduction of the desired carboxylic acid moiety has been achieved through late‐stage TEMPO‐mediated oxidation of the primary OH group on the protected trisaccharide. 1,2‐cis aminoethyl glycoside with central glucosamine is used at the reducing end to the leave the scope for further glycoconjugate formation with suitable aglycone without hampering the anomeric stereochemistry.