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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.

Investigations towards the Synthesis of 5-Amino-l-lyxofuranosides and 4-Amino-lyxopyranosides and NMR Analysis