title: Nucleophilic N1-->N3 rearrangement of 5'-O-trityl-O2,3'-cycloanhydrothymidine.
abstract: 5'-O-Trityl-O2,3'-cycloanhydrothymidine (1) heated at 150 degrees 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.
authors.affiliation: Polish Academy of Sciences, Centre of Molecular and Macromolecular Studies, Lódź.
authors.forename: X B
authors.initials: XB
authors.lastname: Yang
authors.forename: K
authors.initials: K
authors.lastname: Misiura
authors.forename: W J
authors.initials: WJ
authors.lastname: Stec
authors.forename: M J
authors.initials: MJ
authors.lastname: Potrzebowski
authors.forename: S
authors.initials: S
authors.lastname: Kaźmierski
authors.forename: M
authors.initials: M
authors.lastname: Wieczorek
authors.forename: W R
authors.initials: WR
authors.lastname: Majzner
authors.forename: G D
authors.initials: GD
authors.lastname: Bujacz
mesh_terms: D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D009690:Nucleic Acid Conformation; D013936:Thymidine / Q000031:analogs & derivatives / Q000737:chemistry*
chemical_list: C423483:5'-O-trityl-O(2),3'-cycloanhydrothymidine; D013936:Thymidine