Application of NMR spectroscopy for assignment of the absolute configuration of 8-tert -butyl-2-hydroxy-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]dec-6-en-10-one
| Autor: | Anna Jakubowska, Marek Żylewski, Agnieszka Sowa, Katarzyna Kulig |
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| Rok vydání: | 2013 |
| Předmět: |
Pharmacology
Tert butyl Chemistry Stereochemistry Organic Chemistry Absolute configuration Nuclear magnetic resonance spectroscopy Catalysis Analytical Chemistry chemistry.chemical_compound Drug Discovery Molecule Chirality (chemistry) Cyclopentane Two-dimensional nuclear magnetic resonance spectroscopy Spectroscopy |
| Zdroj: | Chirality. 25:422-426 |
| ISSN: | 0899-0042 |
| Popis: | In order to assign the absolute configurations of 8-tert-butyl-2-hydroxy-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]dec-6-en-10-one (2a, 2b), their esters (5a, 5b, 5c, 5d) with (R)- or (S)-2-methoxyphenylacetic acid (4a, 4b) have been synthesized. The absolute configurations of these compounds have been determined on the basis of NOESY correlations between the protons of the tert-butyl group and the cyclopentane fragment of the molecules. The crucial part of this analysis was assignment of the absolute configuration at C-5. Additionally, by calculation of the chemical shift anisotropy, δRS, for the relevant protons, it was also possible to confirm the absolute configurations at the C-2 centres of compounds 2a, 2b and 5a, 5b, 5c, 5d. Chirality, 25:422–426, 2013.© 2013 Wiley Periodicals, Inc. |
| Databáze: | OpenAIRE |
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