Use of 1,3-dibenzyl-dihydrouracil in the chain extension of 2,3-O-isopropylidene-d-glyceraldehyde |
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| Authors: | Fausta UlgheriJohn Bacsa Luigi NassimbeniPietro Spanu |
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| Institution: | a Istituto di Chimica Biomolecolare CNR, Sezione di Sassari Trav. La Crucca 3, Baldinca, 07040 Li Punti Sassari, Italy
b Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa |
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| Abstract: | The aldol-type addition of 1,3-dibenzyl-dihydrouracil 2 to 2,3-O-isopropylidene-d-glyceraldehyde 3 was examined in different solvents and under Lewis acid catalysis in order to establish the stereochemical preferences. A stereodivergent synthesis of 5-trihydroxypropyl-dihydrouracil derivatives 4 and its C-5 epimer 5 was realized. The synthesis of ureido polyols 8 and 10 was obtained via the reductive ring opening of the templates 4 and 5. |
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| Keywords: | dihydrouracil dihydropyrimidin-2 4-dione glyceraldehyde |
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