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Two synthetic phosphonate analogs of lecithin
Author(s) -
Rosenthal Arthur F.,
Pousada Manuel
Publication year - 1969
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02531792
Subject(s) - phosphonate , chemistry , lecithin , ammonium chloride , anhydrous , yield (engineering) , chloride , iodide , glycerol , chromatography , organic chemistry , choline , nuclear chemistry , medicinal chemistry , biochemistry , materials science , metallurgy
The diether‐phosphonate lecithin analog DL‐2‐hexadecoxy‐3‐octadecoxypropyl‐phosphonylcholine was prepared in 55% overall yield by reaction of 2‐hexadecoxy‐3‐octadecoxypropylphosphonic acid with choline iodide and p ‐toluenesulfonyl chloride, and purified chromatographically. The diester‐phosphonate lecithin analog 1,2‐dipalmitoyl‐ sn ‐glycero‐3‐[2′‐trimethyl‐ammonium) ethylphosphonate) was prepared from sn ‐glycerol‐1,2‐dipalmitate and 2‐(trimethylammonium) ethylphosphonyl dichloride, and the reaction mixture purified chromatographically. The lecithin analog was obtained in an anhydrous form.