Cesium carbonate-mediated stereoselective anomeric O-alkylation of a 2N,3O-oxazolidinone-protected d-mannosamine with sugar-derived
primary or secondary alkyl
triflates afforded the corresponding 2-amino-2-deoxy-β-d-mannosides in moderate to good yields and excellent stereoselectivity.
The oxazolidinone ring can be opened with aqueous alkali hydroxide
to liberate the amine functionality. This method has been successfully
applied to the synthesis of the trisaccharide repeating unit of Streptococcus pneumoniae 19F polysaccharide.
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