The synthesis of new 2-phosphono-a-D-glycoside derivatives by stereoselective oxa-Michael addition to an enone derived from D-galactal and containing a phosphonate group is described. Retro-Michael reactions were prevented by tandem acetylation to trap the unstable enolic intermediates. The stereochemistry of the addition products was established by NOESY experiments and explained with molecular mechanics (MM) and density functional theory (DFT) calculations.
Synthesis of new 2-phospono-a-D-glycoside derivatives by stereoselective oxa-Michael addition to a D-galacto derived enone / Leonelli, Francesca; Capuzzi, M; Bodo, Enrico; Passacantilli, Pietro; Piancatelli, Giovanni. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - STAMPA. - 343:(2008), pp. 1133-1141. [10.1016/j.carres.2008.03.009]
Synthesis of new 2-phospono-a-D-glycoside derivatives by stereoselective oxa-Michael addition to a D-galacto derived enone
LEONELLI, Francesca;BODO, Enrico;PASSACANTILLI, Pietro;PIANCATELLI, Giovanni
2008
Abstract
The synthesis of new 2-phosphono-a-D-glycoside derivatives by stereoselective oxa-Michael addition to an enone derived from D-galactal and containing a phosphonate group is described. Retro-Michael reactions were prevented by tandem acetylation to trap the unstable enolic intermediates. The stereochemistry of the addition products was established by NOESY experiments and explained with molecular mechanics (MM) and density functional theory (DFT) calculations.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
