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Tytuł:
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Diastereoselective Synthesis of (1,3-Dioxan-4-yl)pyrimidine and Purin Nucleoside Analogues.
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Autorzy:
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Battisti, Umberto M.
Sorbi, Claudia
Quotadamo, Antonio
Franchini, Silvia
Tait, Annalisa
Schols, Dominique
Jeong, Lak Shin
Lee, Sang Kook
Song, Jayoung
Brasili, Livio
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Temat:
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PYRIMIDINE synthesis
NUCLEOSIDES
PURINES
DIOXANE
SOLVENTS
SINGLE crystals spectra
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Źródło:
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European Journal of Organic Chemistry; Feb2015, Vol. 2015 Issue 6, p1235-1245, 11p
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(1,3-Dioxan-4-yl)-substituted nucleoside analogues, higher homologues of antiviral and anticancer 1,3-dioxolanes, were prepared from the key intermediate (4-acetoxy-1,3-dioxan-2-yl)methyl benzoate and silylated bases. Glycosylation, carried out under Vorbrüggen conditions in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as a catalyst, afforded the desired compounds with high stereoselectivity and regioselectivity, with only the desired β-anomeric N-1 pyrimidine and N-9 purin nucleosides being obtained. 1H NMR experiments established that the β-anomers were diequatorial, and this assignment was confirmed by single-crystal X-ray diffraction. Despite their structural similarities with natural nucleosides, none of the synthesized nucleosides showed antiviral activity. [ABSTRACT FROM AUTHOR]
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