Diastereoselective Synthesis of (1,3-Dioxan-4-yl)pyrimidine and Purin Nucleoside Analogues

Battisti, Umberto M.; Sorbi, Claudia; Quotadamo, Antonio; Franchini, Silvia; Tait, Annalisa; Schols, Dominique; Jeong, Lak Shin; Lee, Sang Kook; Song, Jayoung; Brasili, Livio

doi:10.1002/ejoc.201403473

(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 trimethylsilyltrifluoromethanesulfonate (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 singlecrystal X-ray diffraction. Despite their structural similarities with natural nucleosides, none of the synthesized nucleosides showed antiviral activity.

Diastereoselective Synthesis of (1,3-Dioxan-4-yl)pyrimidine and Purin Nucleoside Analogues / Battisti, Umberto M.; Sorbi, Claudia; Quotadamo, Antonio; Franchini, Silvia; Tait, Annalisa; Schols, Dominique; Jeong, Lak Shin; Lee, Sang Kook; Song, Jayoung; Brasili, Livio. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2015:6(2015), pp. 1235-1245.

Data di pubblicazione:	2015
Titolo:	Diastereoselective Synthesis of (1,3-Dioxan-4-yl)pyrimidine and Purin Nucleoside Analogues
Autore/i:	Battisti, Umberto M.; Sorbi, Claudia; Quotadamo, Antonio; Franchini, Silvia; Tait, Annalisa; Schols, Dominique; Jeong, Lak Shin; Lee, Sang Kook; Song, Jayoung; Brasili, Livio
Autore/i UNIMORE:	Battisti, Umberto M. SORBI, Claudia QUOTADAMO, ANTONIO FRANCHINI, Silvia TAIT, Annalisa Schols, Dominique Jeong, Lak Shin Lee, Sang Kook Song, Jayoung BRASILI, Livio mostra contributor esterni nascondi contributor esterni
Digital Object Identifier (DOI):	http://dx.doi.org/10.1002/ejoc.201403473
Rivista:	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume:	2015
Fascicolo:	6
Pagina iniziale:	1235
Pagina finale:	1245
Codice identificativo ISI:	WOS:000349972700010
Codice identificativo Scopus:	2-s2.0-84922884868
Citazione:	Diastereoselective Synthesis of (1,3-Dioxan-4-yl)pyrimidine and Purin Nucleoside Analogues / Battisti, Umberto M.; Sorbi, Claudia; Quotadamo, Antonio; Franchini, Silvia; Tait, Annalisa; Schols, Dominique; Jeong, Lak Shin; Lee, Sang Kook; Song, Jayoung; Brasili, Livio. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2015:6(2015), pp. 1235-1245.
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