Studies Directed toward the Synthesis of Plasmalogens. I. Alkenylglycerols<sup>1</sup>

Jc, Craig; Dp, Hamon; Hw, Brewer; Haerle, H.

doi:10.1021/jo01014a060

Cited by 20 publications

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“…Alk-1-enyl ethers of dihydric alcohols were detected in hydrolysates of neutral lipids 9 ' 10 . A method described for the preparation of vinyl ethers 11 , adapted to the synthesis of long-chain alk-1-enyl glycerol ethers 12 , was shown 13 to lead to mixtures of racemic l-alk-l'-enyl glycerol ethers and 2-alk-1 '-enyl glycerol ethers, each of which occurs as cis and trans isomers. 9 , but they were not isolated.…”

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confidence: 99%

Alk-1-enyl Ethers of Glycerol and Ethanediol

Baumann¹,

Schmid²,

Kramer³

et al. 1968

Hoppe-Seyler´s Zeitschrift für physiologische Chemie

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Procedures are described for the preparation of neutral aldehydogenic lipids derived from glycerol and ethanediol: Hydrogenolysis of the total lipids of bovine heart muscle with lithium aluminum hydride yields a mixture of lipids from which optically active l-c/'s-alk-l'-enyl glycerol ethers are isolated as a pure lipid class. Periodate oxidation of the alk-1-enyl glycerol ethers and reduction of the intermediate alk-1-enyl glycol-Zusammenfassung: Alkeny lather des Glycerins und Äthandiols. Methoden zur Darstellung neutraler aldehydogener Lipide werden beschrieben: Hydrogenolyse der Gesamtlipide des Rinderherzmuskels mit Lithiumalanat ergibt ein Gemisch von Lipiden, aus dem optisch aktive l-[\-cis-Mkenyl]-glycerinäther als reine Lipidklasse isoliert werden. Perjodatspaltung der Alkenylglycerinäther und Reduktion der intermediär gebildeten Long-chain alk-1-enyl ethers of glycerol occur as constituents of ionic 1 and neutral 2 lipids. Alk-1-enyl acyl glycerophosphatides ("plasmalogens") have not been obtained as pure lipid classes, whereas

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confidence: 99%