Synthesis of heterocyclic platelet activating factor analogues.
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.
Zeidler
J
J
Pharmazeutisches Institut, Universität Tübingen, Germany.
Zimmermann
W
W
D002247:Carbon Isotopes; D009682:Magnetic Resonance Spectroscopy; D010972:Platelet Activating Factor / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011522:Protons
D002247:Carbon Isotopes; D010972:Platelet Activating Factor; D011522:Protons