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19β,28-Epoxy-18α-olean-3β-ol
The title triterpene, C(30)H(50)O(2), is an 18α-oleanane derivative prepared by the Wagner–Meerwein rearrangement of betulin with Bi(OTf)(3).xH(2)O (OTF is trifluoromethanesulfonate). There are two symmetry-independent molecules in the asymmetric unit that show no significant differences concerning...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969885/ https://www.ncbi.nlm.nih.gov/pubmed/21577506 http://dx.doi.org/10.1107/S1600536809030311 |
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author | Santos, R. C. Pinto, R. M. A. Matos Beja, A. Salvador, J. A. R. Paixão, J. A. |
author_facet | Santos, R. C. Pinto, R. M. A. Matos Beja, A. Salvador, J. A. R. Paixão, J. A. |
author_sort | Santos, R. C. |
collection | PubMed |
description | The title triterpene, C(30)H(50)O(2), is an 18α-oleanane derivative prepared by the Wagner–Meerwein rearrangement of betulin with Bi(OTf)(3).xH(2)O (OTF is trifluoromethanesulfonate). There are two symmetry-independent molecules in the asymmetric unit that show no significant differences concerning bond lengths and angles. The conformation of the six-membered rings is close to a chair form, while the five-membered epoxide rings adopt envelope conformations. All rings are trans-fused. In the crystal, molecules are held together by O—H⋯O hydrogen bonds. A quantum-mechanical ab initio Roothan Hartree–Fock calculation on the isolated molecule gives values for bond lengths and valency angles close to the experimental values. The calculations also reproduce well the molecular conformation with calculated puckering parameters that match well the observed values. |
format | Text |
id | pubmed-2969885 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29698852010-12-30 19β,28-Epoxy-18α-olean-3β-ol Santos, R. C. Pinto, R. M. A. Matos Beja, A. Salvador, J. A. R. Paixão, J. A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title triterpene, C(30)H(50)O(2), is an 18α-oleanane derivative prepared by the Wagner–Meerwein rearrangement of betulin with Bi(OTf)(3).xH(2)O (OTF is trifluoromethanesulfonate). There are two symmetry-independent molecules in the asymmetric unit that show no significant differences concerning bond lengths and angles. The conformation of the six-membered rings is close to a chair form, while the five-membered epoxide rings adopt envelope conformations. All rings are trans-fused. In the crystal, molecules are held together by O—H⋯O hydrogen bonds. A quantum-mechanical ab initio Roothan Hartree–Fock calculation on the isolated molecule gives values for bond lengths and valency angles close to the experimental values. The calculations also reproduce well the molecular conformation with calculated puckering parameters that match well the observed values. International Union of Crystallography 2009-08-08 /pmc/articles/PMC2969885/ /pubmed/21577506 http://dx.doi.org/10.1107/S1600536809030311 Text en © Santos et al. 2009 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Santos, R. C. Pinto, R. M. A. Matos Beja, A. Salvador, J. A. R. Paixão, J. A. 19β,28-Epoxy-18α-olean-3β-ol |
title | 19β,28-Epoxy-18α-olean-3β-ol |
title_full | 19β,28-Epoxy-18α-olean-3β-ol |
title_fullStr | 19β,28-Epoxy-18α-olean-3β-ol |
title_full_unstemmed | 19β,28-Epoxy-18α-olean-3β-ol |
title_short | 19β,28-Epoxy-18α-olean-3β-ol |
title_sort | 19β,28-epoxy-18α-olean-3β-ol |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969885/ https://www.ncbi.nlm.nih.gov/pubmed/21577506 http://dx.doi.org/10.1107/S1600536809030311 |
work_keys_str_mv | AT santosrc 19b28epoxy18aolean3bol AT pintorma 19b28epoxy18aolean3bol AT matosbejaa 19b28epoxy18aolean3bol AT salvadorjar 19b28epoxy18aolean3bol AT paixaoja 19b28epoxy18aolean3bol |