Stereoselective synthesis of 3′-substituted 2′-deoxy C-nucleoside pyrazolo[1,5-a]-1,3,5-triazines and their 5′-phosphate nucleotides |
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Authors: | Romain Mathieu Jean-Jacques Bourguignon |
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Institution: | Laboratoire de Pharmacochimie de la Communication Cellulaire (CNRS, UMR 7081), Faculté de Pharmacie, Université Louis Pasteur, 74 route du Rhin, BP60024, 67401 Illkirch cedex, France |
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Abstract: | An efficient synthesis of novel 3′-substituted 2′,3′-dideoxynucleoside analogues in the pyrazolotriazine series was developed from the corresponding 3′-ketonucleoside via the Wittig reaction. On the other hand, a highly stereoselective addition of alkynylcerium reagents to the same precursor led to the 3′-alkynyl-2′-deoxynucleosides in one step with the natural stereochemistry. Applications to produce novel P2Y1 receptor antagonists or new anti-retroviral nucleoside analogues are suggested. |
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Keywords: | C-Nucleoside pyrazolotriazines Nucleotides Wittig reaction Stereoselective addition |
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