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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...

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Autores principales: Santos, R. C., Pinto, R. M. A., Matos Beja, A., Salvador, J. A. R., Paixão, J. A.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
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.
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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
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