Towards validating new enzymatic routes for synthetic conversion: 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetyl baccatin III-ethyl acetate-water (1/1/1)

Acta Crystallogr C Struct Chem. 2015 Mar;71(Pt 3):191-4. doi: 10.1107/S2053229614027399. Epub 2015 Feb 14.

Abstract

The title compound, C(34)H(38)C(l6)O(14)·C(4)H(8)O(2)·H(2)O, prepared by the reaction of 10-deacetyl baccatin III with 2,2,2-trichloroethyl chloroformate in pyridine, crystallizes via strong intermolecular hydrogen bonds and noncovalent interactions between 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetyl baccatin III (7,10-di-Troc-DAB), water and ethyl acetate. A detailed comparison of the molecular conformation with those of related structures is presented.

Keywords: 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetyl baccatin III; Taxol derivative; anticancer agents; biological activity; crystal structure; halogen bonding; natural products; pharmaceutical compounds; taxane diterpenoids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Crystallization
  • Hydrogen Bonding
  • Molecular Conformation
  • Paclitaxel / chemical synthesis*
  • Paclitaxel / chemistry
  • Taxoids / chemical synthesis*
  • Taxoids / chemistry*
  • Water / chemistry*
  • X-Ray Diffraction

Substances

  • 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetyl baccatin III-ethyl acetate
  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Taxoids
  • Water
  • baccatin III
  • Paclitaxel