Structure of a modified nucleoside, 3' alpha-diethylphosphono-3' beta-hydroxy-5'-O-tritylthymidine.
The modified nucleoside of the title was synthesized by nucleophilic addition of lithium diethyl phosphite to the corresponding 3'-keto nucleoside under basic conditions. C--P bond formation resulted from attack on the alpha face, trans to C(5') and the thymine ring. One molecule of EtOH crystallized with the nucleoside (C33H37N2O8P.-C2H6O). Intermolecular hydrogen bonds were observed between the O atom of the alcohol and the O(3')hydroxyl H atom, and between the phosphoryl O atom, O(5), and the N(3) H atom of the thymine ring.
Capron
M A
MA
Department of Chemistry, University of Iowa, Iowa City 52242.
McEldoon
W L
WL
Baenziger
N C
NC
Wiemer
D F
DF
D018360:Crystallography, X-Ray; D015394:Molecular Structure; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry; D014320:Triphenylmethyl Compounds / Q000737:chemistry*
C086709:3'-diethylphosphono-3'-hydroxy-5'-O-tritylthymidine; D014320:Triphenylmethyl Compounds; D013936:Thymidine