Literature DB >> 34925888

Crystal structure of (+)-(1S,5S,6S,7S,10S,11S,16S)-16-hy-droxy-7-(meth-oxy-meth-oxy)-11,15,18,18-tetra-methyl-3,13-dioxo-2,4-dioxa-tetra-cyclo[12.3.1.01,5.06,11]octa-dec-14-en-10-yl benzoate.

Takeshi Oishi1, Keisuke Fukaya2, Takaaki Sato2, Noritaka Chida2.   

Abstract

In the fused tetra-cyclic system of the title compound, C29H36O9, the five-membered dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of the other three atoms by -0.252 (6) and 0.340 (6) Å. The cyclo-hexane, cyclo-hexene and central cyclo-octane rings show chair, half-chair and boat-chair forms, respectively. There are three intra-molecular C-H⋯O inter-actions supporting the mol-ecular conformation, with one S(6) and two S(7) graph-set motifs. In the crystal, inter-molecular O-H⋯O hydrogen bonds connect the mol-ecules into a helical chain running along the c-axis direction, generating a C(7) graph-set motif. The chains are further linked by inter-molecular C-H⋯O inter-actions to construct a three-dimensional network. There is no valid C-H⋯π inter-action. © Oishi et al. 2021.

Entities:  

Keywords:  crystal structure; cyclo­hexa­ne; cyclo­hexene; cyclo­octa­ne; dioxolane; hydrogen bond; paclitaxel; taxane skeleton

Year:  2021        PMID: 34925888      PMCID: PMC8647750          DOI: 10.1107/S2056989021011518

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


  9 in total

1.  Practical synthesis of the C-ring precursor of paclitaxel from 3-methoxytoluene.

Authors:  Keisuke Fukaya; Yu Yamaguchi; Ami Watanabe; Hiroaki Yamamoto; Tomoya Sugai; Takeshi Sugai; Takaaki Sato; Noritaka Chida
Journal:  J Antibiot (Tokyo)       Date:  2016-02-10       Impact factor: 2.649

2.  Formal total synthesis of (-)-taxol through Pd-catalyzed eight-membered carbocyclic ring formation.

Authors:  Sho Hirai; Masayuki Utsugi; Mitsuhiro Iwamoto; Masahisa Nakada
Journal:  Chemistry       Date:  2014-10-24       Impact factor: 5.236

3.  Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2-Mediated Cyclization.

Authors:  Keisuke Fukaya; Yuta Tanaka; Ayako C Sato; Keisuke Kodama; Hirohisa Yamazaki; Takeru Ishimoto; Yasuyoshi Nozaki; Yuki M Iwaki; Yohei Yuki; Kentaro Umei; Tomoya Sugai; Yu Yamaguchi; Ami Watanabe; Takeshi Oishi; Takaaki Sato; Noritaka Chida
Journal:  Org Lett       Date:  2015-05-26       Impact factor: 6.005

4.  Synthesis of Paclitaxel. 2. Construction of the ABCD Ring and Formal Synthesis.

Authors:  Keisuke Fukaya; Keisuke Kodama; Yuta Tanaka; Hirohisa Yamazaki; Tomoya Sugai; Yu Yamaguchi; Ami Watanabe; Takeshi Oishi; Takaaki Sato; Noritaka Chida
Journal:  Org Lett       Date:  2015-05-26       Impact factor: 6.005

5.  SHELXT - integrated space-group and crystal-structure determination.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A Found Adv       Date:  2015-01-01       Impact factor: 2.290

6.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172

7.  Use of intensity quotients and differences in absolute structure refinement.

Authors:  Simon Parsons; Howard D Flack; Trixie Wagner
Journal:  Acta Crystallogr B Struct Sci Cryst Eng Mater       Date:  2013-05-17

8.  The Cambridge Structural Database.

Authors:  Colin R Groom; Ian J Bruno; Matthew P Lightfoot; Suzanna C Ward
Journal:  Acta Crystallogr B Struct Sci Cryst Eng Mater       Date:  2016-04-01

9.  Mercury 4.0: from visualization to analysis, design and prediction.

Authors:  Clare F Macrae; Ioana Sovago; Simon J Cottrell; Peter T A Galek; Patrick McCabe; Elna Pidcock; Michael Platings; Greg P Shields; Joanna S Stevens; Matthew Towler; Peter A Wood
Journal:  J Appl Crystallogr       Date:  2020-02-01       Impact factor: 3.304

  9 in total

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