Ralf Haiges - Structure of Cyclic Nucleoside Phosphonate Ester Prodrugs: An Inquiry.

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  Publication Details (including relevant citation   information): Krylov, Ivan S., Zakharova, Valeria M.,   Serpi, Michaela, Haiges, Ralf, Kashemirov, Boris A., McKenna,   Charles E., J. Org. Chem., 2012,   77 (1), pp 684-689

  Abstract: The configuration at phosphorus in   cyclic (S)-HPMPC (1, cidofovir) and (S)-HPMPA (2) Ph ester (5 and   6, resp.) diastereomers ((Rp)-5, (Rp)-6, (Sp)-6) was detd. by   X-ray crystallog. and correlated to their 1H and 31P NMR spectra   in soln. (Rp)-5 and (Rp)-6 have chair conformations with the   nucleobase substituent equatorial and the P-OPh axial. Perhaps   surprisingly, (Sp)-6 is (a,a) in the crystal and exists largely   as an equil. of (a,a)/(e,e) conformers in chloroform or   acetonitrile. [on SciFinder(R)]

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