Synthesis of 3-(alpha- and beta-D-arabinofuranosyl)-6-chloro-1,2,4-triazolo[4,3-b]pyridazine

Carbohydr Res. 2003 Sep 26;338(20):2057-66. doi: 10.1016/s0008-6215(03)00347-1.

Abstract

Di-O-isopropylidene- and O-methanesulfonyl-protected 1-C-(6-chloro-1,2,4-triazolo[4,3-b]pyridazin-3-yl)pentitols were prepared in three to four steps from D-galactose, D-glucose, D-mannose, and 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose. Acid-catalysed treatment of (1S)- and (1R)-1-C-(6-chloro-1,2,4-triazolo[4,3-b]-pyridazin-3-yl)-2,3:4,5-di-O-isopropylidene-1-O-methanesulfonyl-D-arabinitols in refluxing 1,2-dimethoxyethane furnished 3-(alpha- and beta-D-arabinofuranosyl)-6-chloro-1,2,4-triazolo[4,3-b]pyridazine, respectively. Several structures, including the structure of the 3-(beta-D-arabinofuranosyl)-6-chloro-1,2,4-triazolo[4,3-b]pyridazine, were also determined by single-crystal X-ray diffraction analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arabinose / analogs & derivatives
  • Arabinose / chemical synthesis
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Crystallography, X-Ray
  • Molecular Structure
  • Nucleosides / chemistry*
  • Pyridazines / chemical synthesis
  • Stereoisomerism

Substances

  • 3-arabinofuranosyl-6-chloro-1,2,4-triazolo(4,3-b)pyridazine
  • Nucleosides
  • Pyridazines
  • Arabinose