Synthesis and transport studies of new enantiopure lipophilic crown ethers containing a diarylphosphinic acid unit

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The synthesis of new enantiopure lipophilic crown ethers (S,S)-6, (R,R)-6 and (S,S)-7 containing a diarylphosphinic acid unit has been carried out. The transport ability of these ligands has been studied in an aqueous source phase/lipophilic organic bulk liquid membrane/aqueous receiving phase system controlled by the pH of the media. The transport of metal ions and amines has also been studied. These studies showed high selectivity for protonated amines.

(2S,10S)-2,10-Didecyl-3,6,9-trioxaundecane-1,11-diyl-bis(4-methylbenzenesulfonate)C42H70O9S2Ee > 99%[α]D25 = −4.3 (c 1.77, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (2S,10S)

(2S,13S)-2,13-Didecyl-3,6,9,12-tetraoxatetradecane-1,14-diyl-bis(4-methylbenzenesulfonate)C44H74O10S2Ee > 99%[α]D25 = −4.2 (c 1.07, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (2S,13S)

(7S,15S)-7,15-Didecyl-22-ethoxy-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxa-λ5-phosphacyclooctadecin-22-oneC42H69O7PEe > 99%[α]D25 = −4.8 (c 1.40, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (7S,15S)

(7S,18S)-7,18-Didecyl-25-ethoxy-6,7,9,10,12,13,15,16,18,19-decahydro-25H-dibenzo[q,t][1,4,7,10,13,16,19]hexaoxa-λ5-phosphacyclohenicosin-25-oneC44H73O8PEe > 99%[α]D25 = −14.8 (c 1.00, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (7S,18S)

(R)-Benzyloxy-dodecane-2-olC19H32O2Ee > 99%[α]D25 = −4.5 (c 1.83, CH2Cl2)Source of chirality: (R)-epoxydodecaneAbsolute configuration: (2R)

(2R,10R)-1,11-Bis(benzyloxy)-2,10-didecyl-3,6,9-trioxaundecaneC42H70O5Ee > 99%[α]D25 = +6.8 (c 1.02, CH2Cl2)Source of chirality: (R)-epoxydodecaneAbsolute configuration: (2R,10R)

(2S,13S)-1,14-Bis(benzyloxy)-2,13-didecyl-3,6,9,12-tetraoxatetradecaneC44H74O6Ee > 99%[α]D25 = −5.2 (c 0.98, MeOH)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (2S,13S)

(2S,10S)-2,10-Didecyl-3,6,9-trioxaundecane-1,11-diolC28H58O5Ee > 99%[α]D25 = +4.0 (c 1.50, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (2S,10S)

(2S,13S)-2,13-Didecyl-3,6,9,12-tetraoxatetradecane-1,14-diolC30H62O6Ee > 99%[α]D25 = +4.0 (c 1.50, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (2S,13S)

(7S,15S)-7,15-Didecyl-22-hydroxy-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13,16]pentaoxa-λ5-phosphacyclooctadecin-22-oneC40H65O7PEe > 99%[α]D25 = +33.0 (c 1.01, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (7S,15S)

(7S,18S)-7,18-Didecyl-25-hydroxy-6,7,9,10,12,13,15,16,18,19-decahydro-25H-dibenzo[q,t][1,4,7,10,13,16,19]hexaoxa-λ5-phosphacyclohenicosin-25-oneC42H69O8PEe > 99%[α]D25 = +10.4 (c 1.01, CH2Cl2)Source of chirality: (S)-dodecane-1,2-diolAbsolute configuration: (7S,18S)