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[,5.06,11]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative

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

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4 Citations (Scopus)


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).

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


  • Crystal structure
  • Hydrogen bonds
  • Paclitaxel
  • Taxane skeleton

ASJC Scopus subject areas

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


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