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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...

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Autores principales: Oishi, Takeshi, Fukaya, Keisuke, Yamaguchi, Yu, Sugai, Tomoya, Watanabe, Ami, Sato, Takaaki, Chida, Noritaka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
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).
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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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