Cyclic chiral silyl derivatives for the determination of the absolute configuration of aliphatic diols by gas chromatography

Org Lett. 2002 Aug 22;4(17):2869-71. doi: 10.1021/ol026265v.

Abstract

[reaction: see text] Chiral bidentate silyl reagents have been developed for the GC analysis of aliphatic 1,3- and 1,4-diols. These reagents react with the diols to cyclic siloxanes, which allow the determination of their enantiomeric composition even in complex mixtures. The absolute configuration of 4,6-nonadecanediol 7, occurring in the lipids of sunflower pollen, has been determined to be (4S,6R) by comparison with derivatized synthetic enantiomers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemotactic Factors / chemistry
  • Chromatography, Gas / methods
  • Fatty Alcohols / chemistry*
  • Helianthus / chemistry
  • Lipids / chemistry
  • Pollen / chemistry
  • Silanes / chemistry
  • Stereoisomerism

Substances

  • Chemotactic Factors
  • Fatty Alcohols
  • Lipids
  • Silanes