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Structural Determination of Two Isomers of Betamethasone by NMR Spectroscopy

✍ Scribed by Tze-Ming Chan; C. Anderson Evans; Kimberly A. Belsky; Elizabeth A. Dirnfeld; David J. S. Tsai; Andrew T. McPhail

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
377 KB
Volume
34
Category
Article
ISSN
0749-1581

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✦ Synopsis

Two isomers of betamethasone 9a-fluoro-11~,17a,21-trihydroxy-l6~-methy~pregna-l,4diene-3,2~ione (l), were isolated from the mother liquor of a manufacturing process and were characterized by NMR spectroscopy. They were identified as 8a-fluoro-l1~,17a,2l-trihydroxy-l6~-methyl-9~-pregna-l,4-diene-3,20-dione (2) and 14fkfluoro-11~,17a,21-trihydroxy-l6~-methyl-8a,9~pregna-l,~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.

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