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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| Published in | Tetrahedron: asymmetry Vol. 17; no. 17; pp. 2538 - 2547 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
02.10.2006
Elsevier |
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| Abstract | 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. |
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| AbstractList | 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 dihydrogen-phosphates in low yields. Tetraethylene glycols are reluctant to undergo macrocyclization with phosphorus oxychloride, especially the ones which contain secondary hydroxyl groups. (c) 2006 Elsevier Ltd. All rights reserved. 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. |
| Author | Bertha, Ferenc Sziebert, Dénes Huszthy, Péter Kovács, Ilona |
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| CitedBy_id | crossref_primary_10_1002_ejoc_201101769 crossref_primary_10_1016_j_tet_2008_07_111 crossref_primary_10_1016_j_tet_2019_01_039 crossref_primary_10_1016_j_tetasy_2015_04_015 crossref_primary_10_1016_j_tetasy_2009_11_011 crossref_primary_10_1021_acs_joc_5b00241 crossref_primary_10_1055_s_0040_1707854 crossref_primary_10_1016_j_tetasy_2011_03_011 crossref_primary_10_1016_j_tetasy_2014_10_006 crossref_primary_10_1016_j_tet_2016_11_041 |
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| Keywords | TRANSPORT LIGANDS MACROCYCLES IONOPHORES ENANTIOMERIC RECOGNITION ION PERMEATION SEPARATION PYRIDINO-18-CROWN-6 COMPOSITE MEMBRANES THERMOCONTROL |
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| Snippet | Seven new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety were prepared starting from optically active... |
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| Title | Synthesis of new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety |
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