Synthesis of 2-Amino-2-deoxy-β-d-mannosides via Stereoselective Anomeric O-Alkylation of 2N,3O-Oxazolidinone-Protected d-Mannosamine: Synthesis of the Trisaccharide Repeating Unit of Streptococcus pneumoniae 19F Polysaccharide.
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DOI: 10.1021/acs.orglett.3c01564
Abstract: 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… read more here.
Keywords: anomeric alkylation; oxazolidinone; oxazolidinone protected; synthesis ... See more keywords
Regio- and Stereoselective Synthesis of 1,2- cis-Glycosides by Anomeric O-Alkylation with Organoboron Catalysis.
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DOI: 10.1021/acs.orglett.8b03823
Abstract: Regio- and stereoselective synthesis of 1,2- cis-glycosides has been achieved by catalytic anomeric O-alkylation using organoboron compounds. Modulating steric and electronic factors of both catalysts and substrates enables activation of the axially oriented anomeric oxygens… read more here.
Keywords: anomeric alkylation; cis glycosides; synthesis cis; stereoselective synthesis ... See more keywords