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