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Synthesis of azathia-analogues of platelet activating factor containing a methioninol backbone

✍ Scribed by J.M. Zeidler; W. Zimmermann; H.J. Roth

Publisher: Elsevier Science
Year: 1990
Tongue: English
Weight: 511 KB
Volume: 56
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(90)90100-6

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✦ Synopsis

The synthesis of azathia-analogues of the platelet activating factor containing a methioninol backbone is reported. The preparation starts with acylating methionine ethyl ester-HCl with palmitoyl chloride to form the amide linkage. Following ester reduction the phosphocholine part is introduced via 2-chloro-2-oxo-l,3,2-dioxaphospholane and subsequent ring opening with trimethylamine under pressure. Two related compounds, the sulfoxide and the sulfone, are obtained by oxidation with 3-chloroperbencoic acid. In addition the sulfoxide derivative is prepared starting with d-and/-methionine ethyl ester-HCl.

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