Abstract
Metaperiodate cleavage of the glycerol side chain from an N-acetyl neuraminic acid-derived thioglycoside and condensation with the two enantiomers of the Ellman sulfinamide afford two diastereomeric N-sulfinylimines from which bacterial sialic acid donors with the legionaminic and acetaminic acid configurations and their 8-epi-isomers are obtained by samarium iodide-mediated coupling with acetaldehyde and subsequent manipulations. A variation on the theme, with inversion of the configuration at C5, similarly provides two differentially protected pseudaminic acid donors.
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