| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1389692 | Carbohydrate Research | 2008 | 9 Pages |
Abstract
The synthesis of new 2-phosphono-α-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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Related Topics
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Organic Chemistry
Authors
Francesca Leonelli, Marinella Capuzzi, Enrico Bodo, Pietro Passacantilli, Giovanni Piancatelli,