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Diastereoisomers of a prednisolone derivative

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Abstract

The crystal and molecular structures of two synthetic corticosteroid diastereoisomers were determined by X-ray diffraction methods. (22R)-21-acetoxy-16α,17α-furfurylidenedioxy-11β-hydroxy-pregna-1,4-diene-3,20-dione, C28H32O8, crystallized in the orthorhombic system, space group P212121,a=6.346(1),b=14.106(2),c=27.901(3) Å, andZ=4. (22S)-21-acetoxy-16α, 17α-furfurylidenedioxy-11β-hydroxy-5 pregna-1,4-diene-3,20-dione ethanolate, C28H32O8 ·C2H5OH, crystallized in the monoclinic system, space group C2,a=20.382(5),b=8.331(1),c=17.346(4)Å, β=103.43(2)°, andZ=4. A change of configuration at the C(22) chirality center has influence on the remote parts of the molecules. The long-range effects appear in the ability to form intermolecular hydrogen bonds by different atoms and consequently in the solvation of the (S) diastereoisomer.

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Authors and Affiliations

  1. Institute of Chemistry, Agricultural and Teacher University, 3 Maja 54, 08-110, Siedlce, Poland

    B. Pniewska & W. Kroszczyński

  2. Department of Chemistry, University of Warsaw, Pasteura 1, 02-093, Warszawa, Poland

    R. Anulewicz

  3. Infarm Co. Ltd., Rydygiera 8, 01-793, Warszawa, Poland

    T. Uszycka-Horawa

Authors
  1. B. Pniewska
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  2. R. Anulewicz
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  3. T. Uszycka-Horawa
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  4. W. Kroszczyński
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Pniewska, B., Anulewicz, R., Uszycka-Horawa, T. et al. Diastereoisomers of a prednisolone derivative. J Chem Crystallogr 25, 677–681 (1995). https://doi.org/10.1007/BF01665975

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  • DOI: https://doi.org/10.1007/BF01665975

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