Investigations towards the Synthesis of 5-Amino-l-lyxofuranosides and 4-Amino-lyxopyranosides and NMR AnalysisThis work was supported jointly by the NSF Center for Chemical Evolution, Grant CHE-1504217.
Received: 02 April 2017
Accepted after revision: 12 May 2017
01 June 2017 (online)
The reactivity of trifluoromethanesulfonyl esters derived from l-lyxofuranosides and l-lyxopyranosides was investigated with various 5-aminopyrimidines as nucleophiles with the expectation to synthesize N-substituted 5-amino-ribosugars. The lyxopyranoside forms were found to be unreactive, while the lyxofuranoside forms were found to be reactive with 5-aminopyrimidines, yielding novel N-substituted 5-amino-lyxofuranosides. We report on the synthesis of these novel N-substituted lyxofuranosides and the systematic analyses of NMR data that demonstrate trends within each series: furano-, pyrano-, β- and α- anomers of l-lyxose and β-d-ribopyranoside forms. The data call for caution when identifying these monosaccharides in isomeric mixtures.