Cesium carbonate-mediated anomeric O-alkylation of various protected 2-azido-2-deoxy-D-mannoses with primary triflate electrophiles afforded corresponding 2-azido-2-deoxy-βmannosides in good yields and excellent anomeric selectivity. In addition, 1,3-dibromo-5,5-dimethylhydantoin was found to be the optimal oxidant for preparation of those 2-azido-2-deoxy-Dmannoses from their corresponding thioglycosides. The utilization of this method was demonstrated in the synthesis of a tetrasaccharide fragment of Micrococcus luteus teichuronic acid containing N-acetyl-β-D-mannosaminuronic acid (ManNAcA).
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.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.