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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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Detalles Bibliográficos
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
Descripción
Sumario: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.