Short synthesis of enantiopure C2-symmetric 1,2:4,5-diepoxypentane and "pseudo"-C2-symmetric 3-azido-1,2:4,5-diepoxypentane from arabitol

J Org Chem. 2003 Oct 17;68(21):8252-5. doi: 10.1021/jo034374x.

Abstract

On the basis of our previously described selective protection of arabitol as its 1,2:4,5-bis-pentylidene acetal 5, we report a straightforward synthesis of the novel "pseudo"-C(2)-symmetric 3-azido-1,2:4,5-diepoxypentane building block 4 in 6 steps from arabitol. Using a similar synthetic route, an improved synthesis of the C(2)-symmetrical 1,2:4,5-bis-epoxypentane building block 1 is described, also in 6 steps from arabitol. Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemical synthesis*
  • Azides / chemistry
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Sugar Alcohols / chemistry*

Substances

  • 3-azido-1,2-4,5-diepoxypentane
  • Azides
  • Epoxy Compounds
  • Sugar Alcohols
  • 1,2,4,5-diepoxypentane
  • arabitol