Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,-11 SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetra-cyclo[12.3.1.0<sup>1,5</sup>.0<sup>6,11</sup>]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative

Takeshi Oishi, Keisuke Fukaya, Yu Yamaguchi, Tomoya Sugai, Ami Watanabe, Takaaki Satou, Noritaka Chida, H. Ishida

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The title compounds, C<inf>29</inf>H<inf>38</inf>O<inf>8</inf>·0.25C<inf>5</inf>H<inf>12</inf>, (A), C<inf>29</inf>H<inf>38</inf>O<inf>8</inf>, (B), and C<inf>29</inf>H<inf>36</inf>O<inf>8</inf>, (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).

Original languageEnglish
Pages (from-to)466-472
Number of pages7
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number5
DOIs
Publication statusPublished - 2015 May 1

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Benzoates
seats
Crystal structure
Derivatives
crystal structure
Molecules
rings
Crystals
interactions
Cyclohexane
molecules
Conformations
pentanes
Hydrogen bonds
musculoskeletal system
cyclohexane
crystals
inversions
hydrogen bonds
formal glycol

Keywords

  • Crystal structure
  • Hydrogen bonds
  • Paclitaxel
  • Taxane skeleton

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Science(all)
  • Chemistry(all)

Cite this

@article{1365e6bc32884a68a926741557d99444,
title = "Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,-11 SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetra-cyclo[12.3.1.01,5.06,11]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative",
abstract = "The title compounds, C29H38O8·0.25C5H12, (A), C29H38O8, (B), and C29H36O8, (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).",
keywords = "Crystal structure, Hydrogen bonds, Paclitaxel, Taxane skeleton",
author = "Takeshi Oishi and Keisuke Fukaya and Yu Yamaguchi and Tomoya Sugai and Ami Watanabe and Takaaki Satou and Noritaka Chida and H. Ishida",
year = "2015",
month = "5",
day = "1",
doi = "10.1107/S2056989015006854",
language = "English",
volume = "71",
pages = "466--472",
journal = "Acta Crystallographica Section E: Structure Reports Online",
issn = "1600-5368",
publisher = "International Union of Crystallography",
number = "5",

}

TY - JOUR

T1 - Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,-11 SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetra-cyclo[12.3.1.01,5.06,11]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative

AU - Oishi, Takeshi

AU - Fukaya, Keisuke

AU - Yamaguchi, Yu

AU - Sugai, Tomoya

AU - Watanabe, Ami

AU - Satou, Takaaki

AU - Chida, Noritaka

AU - Ishida, H.

PY - 2015/5/1

Y1 - 2015/5/1

N2 - The title compounds, C29H38O8·0.25C5H12, (A), C29H38O8, (B), and C29H36O8, (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).

AB - The title compounds, C29H38O8·0.25C5H12, (A), C29H38O8, (B), and C29H36O8, (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).

KW - Crystal structure

KW - Hydrogen bonds

KW - Paclitaxel

KW - Taxane skeleton

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U2 - 10.1107/S2056989015006854

DO - 10.1107/S2056989015006854

M3 - Article

VL - 71

SP - 466

EP - 472

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

IS - 5

ER -