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Glyceroamidothiophosphates of cholecalciferol (Vitamin D3)

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Lipids

Abstract

The hexamethyltriamide of phosphorous acid activated by the addition of iodine at the optimum molar ratio 1.05∶0.05 was used as a phosphorylating reagent to synthesize cholecalciferyl-3-0-(N,N-dimethylamido)thiophosphate derivatives of 1,3-benzylidene-rac-glycerol, 1,2-isopropylidene-rac-glycerol, 1,3-dioleoyl-rac-glycerol, and 1,2-dioleoyl-rac-glycerol in a one-pot procedure in high overall yields (81–86%). The compounds represent new model types of phospholipid structures which, in addition to glycerol and a steroid fragment, contain a biologically important linkage other than an oxygen-phosphorus bond.

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Abbreviations

HPLC:

high performance liquid chromatography

NMR:

nuclear magnetic resonance

TLC:

thin-layer chromatography

TMS:

tetramethylsilane

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Authors and Affiliations

  1. Department of Chemical Technology, University of Plavdiv, 24 Tsar Assen Street, 4000, Plovdiv, Bulgaria

    Stephan D. Stamatov

  2. Division of Organic Chemistry 1, University of Lund, Chemical Center, Box 124, 221 00, Lund, Sweden

    Salo Gronowitz

Authors
  1. Stephan D. Stamatov
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  2. Salo Gronowitz
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Stamatov, S.D., Gronowitz, S. Glyceroamidothiophosphates of cholecalciferol (Vitamin D3). Lipids 25, 149–151 (1990). https://doi.org/10.1007/BF02544329

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  • DOI: https://doi.org/10.1007/BF02544329

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