Nucleophilic N1→N3 rearrangement of 5′-O-trityl-O2,3′-cycloanhydrothymidine

Article abstract of DOI:10.1080/15257770008045451

5′-O-Trityl-O²,3′-cycloanhydrothymidine (1) heated at 150°C in the presence of O,O-diethyl phosphate or O,O-diethyl phosphorothioate anions undergoes rearrangement into N³-isomer (2); its structure was established by both advanced NMR methods and X-ray crystallographic studies. The most probable mechanism of 1 → 2 rearrangement relies upon reversibility of glycosidic bond cleavage process.

Full text of DOI:10.1080/15257770008045451

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Nucleophilic N1 → N3 Rearrangement of
5′-O-Trityl-O2,3′-Cycloanhydrothymidine
Xian-Bin Yang a , Konrad Misiura a , Wojciech J. Stec a , Marek J.
Potrzebowski a , Sławomir Kaźmierski a , Michał Wieczorek b ,
Wiesław R. Majzner b & Grzegorz D. Bujacz b
a Polish Academy of Sciences, Centre of Molecular and
Macromolecular Studies, Sienkiewicza 112, 90-363, łódź, Poland
b Technical University in łódź, Institute of General Food Chemistry,
Stefanowskiego 4/10, 90-924, łódź, Poland
Version of record first published: 17 Apr 2008.
To cite this article: Xian-Bin Yang , Konrad Misiura , Wojciech J. Stec , Marek J. Potrzebowski ,
Sławomir Kaźmierski , Michał Wieczorek , Wiesław R. Majzner & Grzegorz D. Bujacz (2000):
Nucleophilic N1 → N3 Rearrangement of 5′-O-Trityl-O2,3′-Cycloanhydrothymidine, Nucleosides,
Nucleotides and Nucleic Acids, 19:10-12, 1657-1673
To link to this article: http://dx.doi.org/10.1080/15257770008045451
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