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ABSTRACT:
SUBMITTER: Krylov IS
PROVIDER: S-EPMC3254244 | biostudies-literature | 2012 Jan
REPOSITORIES: biostudies-literature
Krylov Ivan S IS Zakharova Valeria M VM Serpi Michaela M Haiges Ralf R Kashemirov Boris A BA McKenna Charles E CE
The Journal of organic chemistry 20111130 1
The configuration at phosphorus in cyclic (S)-HPMPC (1, cidofovir) and (S)-HPMPA (2) phenyl ester (5 and 6, respectively) diastereomers ((R(p))-5, (R(p))-6, (S(p))-6) was determined by X-ray crystallography and correlated to their (1)H and (31)P NMR spectra in solution. (R(p))-5 and (R(p))-6 have chair conformations with the nucleobase substituent equatorial and the P-OPh axial. Perhaps surprisingly, (S(p))-6 is (a, a) in the crystal and exists largely as an equilibrium of (a, a)/(e, e) conforme ...[more]