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Diastereoselective Synthesis of (1,3‐Dioxan‐4‐yl)pyrimidine and Purin Nucleoside Analogues
Author(s) -
Battisti Umberto M.,
Sorbi Claudia,
Quotadamo Antonio,
Franchini Silvia,
Tait Annalisa,
Schols Dominique,
Jeong Lak Shin,
Lee Sang Kook,
Song Jayoung,
Brasili Livio
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403473
Subject(s) - chemistry , pyrimidine , trimethylsilyl trifluoromethanesulfonate , nucleoside , stereochemistry , regioselectivity , anomer , glycosylation , stereoselectivity , trimethylsilyl , trifluoromethanesulfonate , catalysis , organic chemistry , biochemistry
(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. 1 H 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.