Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxy-ethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate

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

doi:10.1107/S2056989014026048

Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxy-ethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate

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

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

In the title compound, C₃₆H₄₄O₁₀·C₆H₆, the dioxolane ring adopts an envelope conformation with the C atom bonded to the H atom as the flap, while the cyclohexene and cyclohexane rings are in half-chair and chair conformations, respectively. In the crystal, a pair of O - H⋯O hydrogen bonds with an R₂²(26) graph-set motif connect the benzoate molecules into an inversion dimer. The dimers are linked by a weak C - H⋯O interaction into a tape structure along [011¯]. The benzene molecule links the tapes through C - H⋯O and C - H⋯π interactions, forming a sheet parallel to (100).

Original language	English
Pages (from-to)	8-11
Number of pages	4
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	1
DOIs	https://doi.org/10.1107/S2056989014026048
Publication status	Published - 2015 Jan 1

Keywords

Crystal structure
Hydrogen bonds
Paclitaxel
Taxane skeleton

ASJC Scopus subject areas

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

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Oishi, T., Yamaguchi, Y., Fukaya, K., Sugai, T., Watanabe, A., Sato, T., Chida, N., & Ishida, H. (2015). Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxy-ethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate. Acta Crystallographica Section E: Structure Reports Online, 71(1), 8-11. https://doi.org/10.1107/S2056989014026048

Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxy-ethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate. / Oishi, Takeshi; Yamaguchi, Yuu; Fukaya, Keisuke et al.
In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 1, 01.01.2015, p. 8-11.

Research output: Contribution to journal › Article › peer-review

Oishi, T, Yamaguchi, Y, Fukaya, K, Sugai, T, Watanabe, A, Sato, T, Chida, N & Ishida, H 2015, 'Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxy-ethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate', Acta Crystallographica Section E: Structure Reports Online, vol. 71, no. 1, pp. 8-11. https://doi.org/10.1107/S2056989014026048

Oishi T, Yamaguchi Y, Fukaya K, Sugai T, Watanabe A, Sato T et al. Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxy-ethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate. Acta Crystallographica Section E: Structure Reports Online. 2015 Jan 1;71(1):8-11. doi: 10.1107/S2056989014026048

Oishi, Takeshi ; Yamaguchi, Yuu ; Fukaya, Keisuke et al. / Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxy-ethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate. In: Acta Crystallographica Section E: Structure Reports Online. 2015 ; Vol. 71, No. 1. pp. 8-11.

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title = "Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxy-ethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate",

abstract = "In the title compound, C36H44O10·C6H6, the dioxolane ring adopts an envelope conformation with the C atom bonded to the H atom as the flap, while the cyclohexene and cyclohexane rings are in half-chair and chair conformations, respectively. In the crystal, a pair of O - H⋯O hydrogen bonds with an R22(26) graph-set motif connect the benzoate molecules into an inversion dimer. The dimers are linked by a weak C - H⋯O interaction into a tape structure along [011¯]. The benzene molecule links the tapes through C - H⋯O and C - H⋯π interactions, forming a sheet parallel to (100).",

keywords = "Crystal structure, Hydrogen bonds, Paclitaxel, Taxane skeleton",

author = "Takeshi Oishi and Yuu Yamaguchi and Keisuke Fukaya and Tomoya Sugai and Ami Watanabe and Takaaki Sato and Noritaka Chida and H. Ishida",

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T1 - Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxy-ethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate

AU - Oishi, Takeshi

AU - Yamaguchi, Yuu

AU - Fukaya, Keisuke

AU - Sugai, Tomoya

AU - Watanabe, Ami

AU - Sato, Takaaki

AU - Chida, Noritaka

AU - Ishida, H.

PY - 2015/1/1

Y1 - 2015/1/1

N2 - In the title compound, C36H44O10·C6H6, the dioxolane ring adopts an envelope conformation with the C atom bonded to the H atom as the flap, while the cyclohexene and cyclohexane rings are in half-chair and chair conformations, respectively. In the crystal, a pair of O - H⋯O hydrogen bonds with an R22(26) graph-set motif connect the benzoate molecules into an inversion dimer. The dimers are linked by a weak C - H⋯O interaction into a tape structure along [011¯]. The benzene molecule links the tapes through C - H⋯O and C - H⋯π interactions, forming a sheet parallel to (100).

AB - In the title compound, C36H44O10·C6H6, the dioxolane ring adopts an envelope conformation with the C atom bonded to the H atom as the flap, while the cyclohexene and cyclohexane rings are in half-chair and chair conformations, respectively. In the crystal, a pair of O - H⋯O hydrogen bonds with an R22(26) graph-set motif connect the benzoate molecules into an inversion dimer. The dimers are linked by a weak C - H⋯O interaction into a tape structure along [011¯]. The benzene molecule links the tapes through C - H⋯O and C - H⋯π interactions, forming a sheet parallel to (100).

KW - Crystal structure

KW - Hydrogen bonds

KW - Paclitaxel

KW - Taxane skeleton

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Crystal structure of (±)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxy-ethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate

Abstract

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