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Synthesis of azide and amide analogs of platelet-activating factor and related derivatives

✍ Scribed by M.M. Ponpipom; R.L. Bugianesi

Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
428 KB
Volume
35
Category
Article
ISSN
0009-3084

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✦ Synopsis

2-Azido-2-deoxy-l-O-hexadecyl-sn-glycero-3-phosphorylcholine

was prepared in good yield from D-mannitol via 3-O-hexadecyl-2-O-methanesulfonyl-l-O-triphenylmethyl-sn-glycerol. Nucleophilic displacement of the 2-methanesulfonate function by benzoate or azide ion proceeded with inversion of configuration (Sn2) without racemization. Hydrogenation of the azidophospholipid gave 2-amino-2-deoxy-l-O-hexadecyl-sn-glycero-3-phosphorylcholine which is a versatile intermediate for the preparation of amide analogs of platelet-activating factor and related derivatives. The synthesis of 2-deoxy-2-fluoro-l-O-hexadecyl-sn-glycero-3-phosphorylcholine was also described.

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