1027832-07-0Relevant academic research and scientific papers
Ring-expanded nucleoside analogues. 1,3-Dioxan-5-yl pyrimidines
Cadet, Gina,Chan, Ching-See,Daniel, Rose Y.,Davis, Claudette P.,Guiadeen, Deodialsingh,Rodriguez, George,Thomas, Tamara,Walcott, Sean,Scheiner, Peter
, p. 4574 - 4580 (2007/10/03)
1,3-Dioxan-5-yl pyrimidine nucleoside analogues, higher homologues of antiviral and anticancer 1,3-dioxolanes, were prepared from bis-1,3- tritylglycerol and 3-benzoylated bases (uracil, 5-fluorouracil, thymine). Mitsunobu condensation, deprotection, and cycloacetalization gave cis/trans mixtures of 2,5-disubstituted-1,3-dioxanes in which the desired cis stereoisomers predominated. Cytosine derivatives could not be obtained in this manner; N4-benzoylcytosine afforded an O-2 alkylated Mitsunobu product that rearranged to an O2-(2,3-dihydroxypropyl)cytosine on detritylation with aqueous acetic acid. Cytosine and 5-fluorocytosine nucleosides were therefore prepared from the corresponding uracils via their 1,2-4-triazole derivatives. 1H NMR data established the conformational preference for equatorial 2'- hydroxymethyl and axial 5'-base in the cis isomers; the trans compounds were diequatorial. Despite their conformations, the cis nucleosides showed no antiviral activity.
