Bi- and tricyclic compounds were synthesized starting from fructose. The different hydroxyl groups present in fructose were exploited in the formation of a number of conformationally constrained sugar-based scaffolds, including azido acids. Introduction of an azido group and carboxy terminus into different bicyclic iodo ethers, allowed the synthesis of different conformationally constrained azido acids. Conformational analysis of compounds 10, 11, 17, and 20 by NMR experiments assisted by molecular mechanics, allowed the determination of the distances between the relevant functional groups, that is the azido and carboxy functionalities.
Cipolla, L., Forni, E., Jiménez Barbero, J., Nicotra, F. (2002). Synthesis and Conformational analysis of fructose-derived scaffolds: molecular diversity from a single molecole. CHEMISTRY-A EUROPEAN JOURNAL, 8(17), 3976-3983 [10.1002/1521-3765(20020902)8:17<3976::AID-CHEM3976>3.0.CO;2-7].
Synthesis and Conformational analysis of fructose-derived scaffolds: molecular diversity from a single molecole
CIPOLLA, LAURA FRANCESCA;NICOTRA, FRANCESCO
2002
Abstract
Bi- and tricyclic compounds were synthesized starting from fructose. The different hydroxyl groups present in fructose were exploited in the formation of a number of conformationally constrained sugar-based scaffolds, including azido acids. Introduction of an azido group and carboxy terminus into different bicyclic iodo ethers, allowed the synthesis of different conformationally constrained azido acids. Conformational analysis of compounds 10, 11, 17, and 20 by NMR experiments assisted by molecular mechanics, allowed the determination of the distances between the relevant functional groups, that is the azido and carboxy functionalities.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.