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Synthesis of heterocyclic platelet activating factor analogues

✍ Scribed by Jürgen Zeidler; Werner Zimmermann

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
681 KB
Volume
75
Category
Article
ISSN
0009-3084

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✦ Synopsis

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.

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