Synthesis of the Repeating Unit of the Capsular Polysaccharide of Streptococcus Pneumoniae Type 3 as a Building Block Suitable for Formation of Oligomers

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Abstract
The synthesis of a cellobiouronic thioglycoside donor 12, protected with a selectively removable 3′-O-benzyl group is described. The donor 12 is suitable as a monomer building block in the construction of oligomer structures corresponding to the capsular polysaccharide of Streptococcus pneumoniae type 3. The carboxyl function was introduced through regioselective TEMPO-oxidation of a 4′,6′-diol cellobiose derivative. If the oxidation was performed on a 2,3,2′,3′,4′,6′-hexaol derivative, oxidation also of the secondary 2- and 3-hydroxyl groups was observed to give a tricarboxyl derivative as one of the major products. The thioglycoside was formed by acidic mercaptolysis of a 1,6-anhydro bridge. The donor 12 was transformed into a suitable starting monomer acceptor through glycosylation with a spacer alcohol and subsequent debenzylation.

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