Abstract
Total chemical synthesis of the linear tetrasaccharide repeating unit β-D-Glc-(1 → 2)-α-L-Rha-(1 → 3)-α-L-Rha-(1 → 2)-α-L-Rha-CH2CH2NH2 of the O-antigen from Azospirillum brasilense Jm125A2 is accomplished through rational protecting group manipulations of commercially available monosaccharides and stereoselective glycosylations. The target tetrasaccharide in the form of its 2-aminoethyl glycoside is obtained in ∼24% yield over 10 steps following a linear strategy. The structure is particularly suitable for further glycoconjugate formation through the terminal free amine without hampering the reducing end stereochemistry.
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