The synthesis of an isosteric phosphonic acid analogue of platelet activating factor and related materials.
Item
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Title
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The synthesis of an isosteric phosphonic acid analogue of platelet activating factor and related materials.
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Identifier
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AAI9405552
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identifier
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9405552
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Creator
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Liu, Yue-jin.
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Contributor
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Adviser: Robert Engel
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Date
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1993
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Language
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English
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Publisher
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City University of New York.
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Subject
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Chemistry, Organic | Chemistry, Analytical | Chemistry, Biochemistry
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Abstract
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The main purpose of this thesis was the development of optically active structural analogues of platelet activating factor (PAF) which could be used as probes of biological activity. Of interest in the present work are phosphonate analogues of PAF in which a methylene group has been substituted for the esteric oxygen of a phosphate ester. The carbon-phosphorus bond of the phosphonate is not subject to hydrolysis by enzymes involved in the normal cleavage of phosphate esters.;Syntheses of the analogues of platelet activating factor involved a regioselective epoxide-ring opening procedure. The regioselective ring opening of various epoxy derivatives has been studied in the presence of boron trifluoride etherate, and is reported in this dissertation. In the acid catalyzed epoxide ring opening process, alcohols exhibited a notable regioselectivity, attacking the terminal carbon of the epoxy functional group preferentially.;(S)-3-acetyl-4-Octadecanyloxybutane-1-phosphonate choline and (S)-(E)-3-acetyl-4-octadecanyloxybut-{dollar} 1{dollar}-enyl-1-phosphonate choline have been synthesized via regioselective epoxy-ring opening of the suitable butanetriol derivatives. Also, some other epoxy-ring opening reactions have been studied using the boron trifluoride etherate catalyst.
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Type
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dissertation
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Source
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PQT Legacy CUNY.xlsx
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degree
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Ph.D.
