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Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative
The title compounds, C(29)H(38)O(8)·0.25C(5)H(12), (A), C(29)H(38)O(8), (B), and C(29)H(36)O(8), (C), are tetracyclic benzoates possessing a taxane skeleton with a fused dioxolane ring as the core structure. In the asymmetric unit of (A), there are two independent benzoate molecules (A and A′) and...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4420046/ https://www.ncbi.nlm.nih.gov/pubmed/25995857 http://dx.doi.org/10.1107/S2056989015006854 |
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author | Oishi, Takeshi Fukaya, Keisuke Yamaguchi, Yu Sugai, Tomoya Watanabe, Ami Sato, Takaaki Chida, Noritaka |
author_facet | Oishi, Takeshi Fukaya, Keisuke Yamaguchi, Yu Sugai, Tomoya Watanabe, Ami Sato, Takaaki Chida, Noritaka |
author_sort | Oishi, Takeshi |
collection | PubMed |
description | The title compounds, C(29)H(38)O(8)·0.25C(5)H(12), (A), C(29)H(38)O(8), (B), and C(29)H(36)O(8), (C), are tetracyclic benzoates possessing a taxane skeleton with a fused dioxolane ring as the core structure. In the asymmetric unit of (A), there are two independent benzoate molecules (A and A′) and a half molecule of solvent pentane disordered about an inversion center. The molecular conformations of (A), (B) and (C) are similar except for the flexible methoxymethoxy group. The cyclohexane, cyclohexene and central cyclooctane rings adopt chair, half-chair and chair–chair (extended crown) forms, respectively. The dioxolane rings are essentially planar, while the dioxolane ring of A′ is slightly twisted from the mean plane. In the crystal of (A), intermolecular O—H⋯O, C—H⋯O and C—H⋯π interactions link the independent benzoates alternately, forming a chain structure. In the crystals of (B) and (C), molecules are linked through O—H⋯O and C—H⋯π interactions, and C—H⋯O hydrogen bonds, respectively, into similar chains. Further, weak intermolecular C—H⋯O interactions connect the chains into a three-dimensional network in (A) and a sheet in (B), whereas no other interactions are observed for (C). |
format | Online Article Text |
id | pubmed-4420046 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-44200462015-05-20 Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative Oishi, Takeshi Fukaya, Keisuke Yamaguchi, Yu Sugai, Tomoya Watanabe, Ami Sato, Takaaki Chida, Noritaka Acta Crystallogr E Crystallogr Commun Research Communications The title compounds, C(29)H(38)O(8)·0.25C(5)H(12), (A), C(29)H(38)O(8), (B), and C(29)H(36)O(8), (C), are tetracyclic benzoates possessing a taxane skeleton with a fused dioxolane ring as the core structure. In the asymmetric unit of (A), there are two independent benzoate molecules (A and A′) and a half molecule of solvent pentane disordered about an inversion center. The molecular conformations of (A), (B) and (C) are similar except for the flexible methoxymethoxy group. The cyclohexane, cyclohexene and central cyclooctane rings adopt chair, half-chair and chair–chair (extended crown) forms, respectively. The dioxolane rings are essentially planar, while the dioxolane ring of A′ is slightly twisted from the mean plane. In the crystal of (A), intermolecular O—H⋯O, C—H⋯O and C—H⋯π interactions link the independent benzoates alternately, forming a chain structure. In the crystals of (B) and (C), molecules are linked through O—H⋯O and C—H⋯π interactions, and C—H⋯O hydrogen bonds, respectively, into similar chains. Further, weak intermolecular C—H⋯O interactions connect the chains into a three-dimensional network in (A) and a sheet in (B), whereas no other interactions are observed for (C). International Union of Crystallography 2015-04-09 /pmc/articles/PMC4420046/ /pubmed/25995857 http://dx.doi.org/10.1107/S2056989015006854 Text en © Oishi et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Oishi, Takeshi Fukaya, Keisuke Yamaguchi, Yu Sugai, Tomoya Watanabe, Ami Sato, Takaaki Chida, Noritaka Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative |
title | Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative |
title_full | Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative |
title_fullStr | Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative |
title_full_unstemmed | Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative |
title_short | Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative |
title_sort | crystal structures of (±)-(1sr,5sr,6sr,7sr,10sr,11sr,13rs,14sr)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0(1,5).0(6,11)]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4420046/ https://www.ncbi.nlm.nih.gov/pubmed/25995857 http://dx.doi.org/10.1107/S2056989015006854 |
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