Synthesis of new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety

Seven new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety were prepared starting from optically active dialkyl-substituted oligoethylene glycols and phosphorus oxychloride followed by mild hydrolysis of the resulting macrocyclic chlorophosphates. Pentaethylene...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 17; no. 17; pp. 2538 - 2547
Main Authors Kovács, Ilona, Huszthy, Péter, Bertha, Ferenc, Sziebert, Dénes
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.10.2006
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
TRANSPORT
LIGANDS
MACROCYCLES
IONOPHORES
ENANTIOMERIC RECOGNITION
ION PERMEATION
SEPARATION
PYRIDINO-18-CROWN-6
COMPOSITE MEMBRANES
THERMOCONTROL
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Summary:Seven new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety were prepared starting from optically active dialkyl-substituted oligoethylene glycols and phosphorus oxychloride followed by mild hydrolysis of the resulting macrocyclic chlorophosphates. Pentaethylene glycols having primary hydroxyl groups gave good yields of 17-crown-6 type ethers. Pentaethylene glycols with secondary hydroxyl groups rendered about the same amount of 17-crown-6 ethers and open chain dihydrogenphosphates in low yields. Tetraethylene glycols are reluctant to undergo macrocyclization with phosphorus oxychloride, especially the ones which contain secondary hydroxyl groups.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2006.09.018