Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetate
The structure of the title steroid [alternative name: 3β,6β-diacetoxy-5β-methyl-19-norcholest-9(10)-ene], C31H50O4, confirms the generally accepted mechanism for the rearrangement of a cholestan-5α-ol derivative reported a century ago by Westphalen...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2012-12-01
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| Series: | Acta Crystallographica Section E |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S1600536812045278 |
| _version_ | 1818085686139420672 |
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| author | Johana Ramírez Hernández Jesús Sandoval-Ramírez Socorro Meza-Reyes José Luis Vega Báez Sylvain Bernès |
| author_facet | Johana Ramírez Hernández Jesús Sandoval-Ramírez Socorro Meza-Reyes José Luis Vega Báez Sylvain Bernès |
| author_sort | Johana Ramírez Hernández |
| collection | DOAJ |
| description | The structure of the title steroid [alternative name: 3β,6β-diacetoxy-5β-methyl-19-norcholest-9(10)-ene], C31H50O4, confirms the generally accepted mechanism for the rearrangement of a cholestan-5α-ol derivative reported a century ago by Westphalen. The methyl group at position 10 of the starting material migrates to position 5 in the steroidal nucleus, while a Δ9 bond is formed, as indicated by the C=C bond length of 1.347 (4) Å. The methyl transposition leaves the 5R configuration unchanged, with the methyl oriented towards the β face. During the rearrangement, the steroidal B ring experiences a conformational distortion from chair to envelope with the C atom at position 6 as the flap. In the title structure, the isopropyl group of the side chain is disordered over two positions, with occupancies of 0.733 (10) and 0.267 (10). The carbonyl O atom in the acetyl group at C3 is also disordered with an occupancy ratio of 0.62 (4):0.38 (4). |
| first_indexed | 2024-12-10T20:13:43Z |
| format | Article |
| id | doaj.art-5814cb3347ad4bc19905fee6a8a5c371 |
| institution | Directory Open Access Journal |
| issn | 1600-5368 |
| language | English |
| last_indexed | 2024-12-10T20:13:43Z |
| publishDate | 2012-12-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E |
| spelling | doaj.art-5814cb3347ad4bc19905fee6a8a5c3712022-12-22T01:35:14ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682012-12-016812o3331o333110.1107/S1600536812045278Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetateJohana Ramírez HernándezJesús Sandoval-RamírezSocorro Meza-ReyesJosé Luis Vega BáezSylvain BernèsThe structure of the title steroid [alternative name: 3β,6β-diacetoxy-5β-methyl-19-norcholest-9(10)-ene], C31H50O4, confirms the generally accepted mechanism for the rearrangement of a cholestan-5α-ol derivative reported a century ago by Westphalen. The methyl group at position 10 of the starting material migrates to position 5 in the steroidal nucleus, while a Δ9 bond is formed, as indicated by the C=C bond length of 1.347 (4) Å. The methyl transposition leaves the 5R configuration unchanged, with the methyl oriented towards the β face. During the rearrangement, the steroidal B ring experiences a conformational distortion from chair to envelope with the C atom at position 6 as the flap. In the title structure, the isopropyl group of the side chain is disordered over two positions, with occupancies of 0.733 (10) and 0.267 (10). The carbonyl O atom in the acetyl group at C3 is also disordered with an occupancy ratio of 0.62 (4):0.38 (4).http://scripts.iucr.org/cgi-bin/paper?S1600536812045278 |
| spellingShingle | Johana Ramírez Hernández Jesús Sandoval-Ramírez Socorro Meza-Reyes José Luis Vega Báez Sylvain Bernès Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetate Acta Crystallographica Section E |
| title | Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetate |
| title_full | Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetate |
| title_fullStr | Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetate |
| title_full_unstemmed | Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetate |
| title_short | Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetate |
| title_sort | westphalen s diol diacetate 19 10 amp 8594 5 abeo 5 amp 946 cholest 9 ene 3 amp 946 6 amp 946 diyl diacetate |
| url | http://scripts.iucr.org/cgi-bin/paper?S1600536812045278 |
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