Synthesis of azide and amide analogs of platelet-activating factor and related derivatives |
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Authors: | M.M. Ponpipom R.L. Bugianesi |
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Affiliation: | Merck Sharp and Dohme Research Laboratories, P.O. Box 2000, Rahway, NJ 07065, U.S.A. |
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Abstract: | 2-Azido-2-deoxy-1-O-hexadecyl-sn-glycero-3-phosphorylcholine was prepared in good yield from D-mannitol via 3-O-hexadecyl-2-O-methanesulfonyl-1-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-1-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-1-O-hexadecyl-sn-glycero-3-phosphorylcholine was also described. |
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Keywords: | ether-linked phospholipids azide amide analogs of platelet-activating factor acether nucleophilic displacement chemical synthesis |
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