1,720,968 research outputs found

    Stereoselective Michael-Type Addition of Organocopper Reagents to Enones Derived from Glycals in the Synthesis of 2-Phosphono-a-C-Glycosides

    No full text
    Michael-type additions of various organocopper reagents to the novel carbohydrate-derived 2-(diethoxyphosphoryl)hex- 1-en-3-uloses are described. The reactions have proved to be rapid, clean and stereoselective, giving rise to the formation of 3-oxo-2-phosphono-?-C-glycosides or the corresponding enol acetates. These compounds are direct precursors of 2- phosphono-?-C-glycosides, a very interesting class of molecules never described before

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

    No full text
    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
    corecore