Nucleophilic N1 → N3 Rearrangement of 5′-O-Trityl-O2,3′-Cycloanhydrothymidine

Nucleophilic N1 → N3 Rearrangement of 5′-O-Trityl-O2,3′-Cycloanhydrothymidine

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

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Veröffentlicht in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2000-10, Vol.19 (10-12), p.1657-1673
Hauptverfasser: Yang, Xian-Bin, Misiura, Konrad, Stec, Wojciech J., Potrzebowski, Marek J., Kaźmierski, Sławomir, Wieczorek, Michał, Majzner, Wiesław R., Bujacz, Grzegorz D.
Format: Artikel
Sprache:eng
Schlagworte:
Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Nucleic Acid Conformation
Thymidine - analogs & derivatives
Thymidine - chemistry
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Zusammenfassung:5′-O-Trityl-O 2 ,3′-cycloanhydrothymidine (1) heated at 150°C in the presence of O,O-diethyl phosphate or O,O-diethyl phosphorothioate anions undergoes rearrangement into N 3 -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.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770008045451