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Synthesis of acetal and phosphocyclic methriolipids

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Abstract

The first representatives of acetal and phosphocyclic lipids based on methriol (2-hydroxymethyl-2-methyl-1,3-propanediol) were synthesized. The interaction of the starting triol with higher aldehydes gave the corresponding alkylidene compounds, which were subsequently phosphorylated by derivatives of phosphorous acid. The intermediate amidophosphites were treated without isolation with iodobenzene, sulfur, or selenium to give phosphoacetals and their thio-and selenoanalogues, which are acetal phospholipids. Methriol bicyclophosphite was also used in the lipid synthesis. It was acylated with palmitoyl chloride at one of the bicyclic oxygen atoms. Alcoholysis of acyl polyol chlorophosphite resulted in a phospholipid, which was oxidized with sulfur to give thionphosphate.

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Authors and Affiliations

  1. Volgograd State Pedagogical University, pr. Lenina 27, Volgograd, 400131, Russia

    G. A. Savin

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  1. G. A. Savin
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Correspondence to G. A. Savin.

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Original Russian Text © G.A. Savin, 2008, published in Bioorganicheskaya Khimiya, 2008, Vol. 34, No. 6, pp. 822–826.

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Savin, G.A. Synthesis of acetal and phosphocyclic methriolipids. Russ J Bioorg Chem 34, 739–742 (2008). https://doi.org/10.1134/S1068162008060149

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  • DOI: https://doi.org/10.1134/S1068162008060149

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