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Structural determination of two isomers of betamethasone by NMR spectroscopy

Publication ,  Journal Article
Chan, TM; Evans, CA; Belsky, KA; Dirnfeld, EA; Tsai, DJS; McPhail, AT
Published in: Magnetic Resonance in Chemistry
January 1, 1996

Two isomers of betamethasone 9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4- diene-3,20-dione (1), were isolated from the mother liquor of a manufacturing process and were characterized by NMR spectroscopy. They were identified as 8α-fluoro-11β,17α,21-trihydroxy-16β-methyl-9β-pregna- 1,4-diene-3,20-dione (2) and 14β-fluoro-11β,17α,21-trihydroxy-16β-methyl-8α, 9β-pregna-1,4-diene-3,20-dione (3). The stereochemistries of 2 and 3 were assigned on the basis of proton-proton and proton-fluorine NOE experiments. The structure of the former was confirmed by x-ray crystallographic analysis.

Duke Scholars

Published In

Magnetic Resonance in Chemistry

DOI

ISSN

0749-1581

Publication Date

January 1, 1996

Volume

34

Issue

12

Start / End Page

1025 / 1030

Related Subject Headings

  • Physical Chemistry
  • 3406 Physical chemistry
  • 0306 Physical Chemistry (incl. Structural)
  • 0304 Medicinal and Biomolecular Chemistry
 

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Chan, T. M., Evans, C. A., Belsky, K. A., Dirnfeld, E. A., Tsai, D. J. S., & McPhail, A. T. (1996). Structural determination of two isomers of betamethasone by NMR spectroscopy. Magnetic Resonance in Chemistry, 34(12), 1025–1030. https://doi.org/10.1002/(SICI)1097-458X(199612)34:12<1025::AID-OMR14>3.0.CO;2-V
Chan, T. M., C. A. Evans, K. A. Belsky, E. A. Dirnfeld, D. J. S. Tsai, and A. T. McPhail. “Structural determination of two isomers of betamethasone by NMR spectroscopy.” Magnetic Resonance in Chemistry 34, no. 12 (January 1, 1996): 1025–30. https://doi.org/10.1002/(SICI)1097-458X(199612)34:12<1025::AID-OMR14>3.0.CO;2-V.
Chan TM, Evans CA, Belsky KA, Dirnfeld EA, Tsai DJS, McPhail AT. Structural determination of two isomers of betamethasone by NMR spectroscopy. Magnetic Resonance in Chemistry. 1996 Jan 1;34(12):1025–30.
Chan, T. M., et al. “Structural determination of two isomers of betamethasone by NMR spectroscopy.” Magnetic Resonance in Chemistry, vol. 34, no. 12, Jan. 1996, pp. 1025–30. Scopus, doi:10.1002/(SICI)1097-458X(199612)34:12<1025::AID-OMR14>3.0.CO;2-V.
Chan TM, Evans CA, Belsky KA, Dirnfeld EA, Tsai DJS, McPhail AT. Structural determination of two isomers of betamethasone by NMR spectroscopy. Magnetic Resonance in Chemistry. 1996 Jan 1;34(12):1025–1030.
Journal cover image

Published In

Magnetic Resonance in Chemistry

DOI

ISSN

0749-1581

Publication Date

January 1, 1996

Volume

34

Issue

12

Start / End Page

1025 / 1030

Related Subject Headings

  • Physical Chemistry
  • 3406 Physical chemistry
  • 0306 Physical Chemistry (incl. Structural)
  • 0304 Medicinal and Biomolecular Chemistry