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Diastereoselective synthesis of d-xylo-isoxazolidinyl nucleosides |
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| Authors: | Eva Hýrošová Lubor Fišera Christian Hametner Martina Marchetti |
| Institution: | a Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinskeho 9, 81237 Bratislava, Slovak Republic b Institute of Applied Synthetic Chemistry, University of Technology, A-1060 Vienna, Austria c Institute of Chemical Technologies and Analytics, University of Technology, A-1060 Vienna, Austria |
| Abstract: | The condensation of the acetoxyisoxazolidines with silylated uracil, thymine, cytosine, N-acetylcytosine, and guanine proceeded in good yields and with moderate to good stereoselectivity to give isoxazolidinyl β- and α-nucleosides. The stereoselectivity of the addition is dependent on the structure of the substituent at C-3 originating from the starting chiral nitrone. The Vorbrüggen nucleosidation of isoxazolidine 8 at 70 °C afforded β-anomers as the exclusive nucleosides together with the isoxazoline 11. It was found that the nucleosidation proceeded also in methylene chloride at room temperature. |
| Keywords: | Nucleosides 1 3-Dipolar cycloaddition C-Glycosyl nitrones |
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