Synthesis of heterocyclic platelet activating factor analogues

Chem Phys Lipids. 1994 Oct 20;74(1):73-81. doi: 10.1016/0009-3084(94)90113-9.

Abstract

The synthesis of heterocyclic analogues of the platelet activating factor is described. The preparation starts with acylating rac-tetrahydro-1,3-thiazine-4-carboxylic acid ethyl ester, with palmitoyl chloride to form the amide linkage. Following ester reduction, the phosphocholine part is introduced via 2-chloro-2-oxo-1,3,2-dioxaphospholane and subsequent ring opening with trimethylamine under pressure. Furthermore, the related L-thiazolidine analogue is prepared using the same procedure. In addition the sulfinyl and sulfonyl derivatives of this compound are obtained by oxidation with 3-chloro-perbencoic acid. From one sulfinyl intermediate the diastereomeres are separated and their conformations are determinated by 13C-NMR spectroscopy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon Isotopes
  • Magnetic Resonance Spectroscopy
  • Platelet Activating Factor / analogs & derivatives*
  • Platelet Activating Factor / chemical synthesis
  • Protons

Substances

  • Carbon Isotopes
  • Platelet Activating Factor
  • Protons