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. 2008 May 19;343(7):1133-41.
doi: 10.1016/j.carres.2008.03.009. Epub 2008 Mar 13.

Synthesis of new 2-phosphono-alpha-D-glycoside derivatives by stereoselective oxa-Michael addition to a D-galacto derived enone

Francesca Leonelli  1 , Marinella Capuzzi, Enrico Bodo, Pietro Passacantilli, Giovanni Piancatelli
Affiliations

Synthesis of new 2-phosphono-alpha-D-glycoside derivatives by stereoselective oxa-Michael addition to a D-galacto derived enone

Francesca Leonelli et al. Carbohydr Res. .

Abstract

The synthesis of new 2-phosphono-alpha-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.

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