Synthesis of a spacer-containing nonasaccharide fragment of Streptococcus pneumoniae 19F capsular polysaccharide

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Abstract
The nonasaccharide 1, representing three repeating units of the capsular polysaccharide from Streptococcus pneumoniae 19F, has been synthesized. The synthetic strategy is to first synthesize, by an AB + C route, trisaccharide derivative 14, having O-benzyl groups as persistent, and 1-O-allyl and 4″-O-acetyl groups as temporary, protecting groups. Then, specific replacement of the 1-O-allyl group with an α-H-phosphonate monoester gives trisaccharide 17, which is coupled to a spacer. The obtained derivative 18 is then extended from the 4″ end in a stepwise fashion to give compound 20, using trisaccharide 17 and solution-phase H-phosphonate chemistry. Finally, removal of the persistent O-protecting groups gives the nonasaccharide 1.

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