title: Synthesis of heterocyclic platelet activating factor analogues.
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.
authors.affiliation: Pharmazeutisches Institut, Universität Tübingen, Germany.
authors.forename: J
authors.initials: J
authors.lastname: Zeidler
authors.forename: W
authors.initials: W
authors.lastname: Zimmermann
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010972:Platelet Activating Factor / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D010972:Platelet Activating Factor