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Triester glycerothiophosphates of cholecalciferol (vitamin D 3 )
Author(s) -
Stamatov Stephan D.,
Gronowitz Salo
Publication year - 1992
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/bf02536388
Subject(s) - chemistry , reagent , alcohol , glycerol , amide , organic chemistry , medicinal chemistry
Tris(N,N ‐dimethyl)amide of phosphorous acid activated by addition of iodine at an optimal molar ratio of 1.05∶0.05 was used as a phosphorylating reagent to synthesize cholecalciferyl‐3‐ O ‐(1‐2‐isopropylidene‐ rac ‐glycero‐3‐ O ‐)‐thiophosphate and cholecalciferyl‐3‐ O ‐(1,2‐dipalmitoyl‐ rac ‐glycero‐3‐ O ‐)thiophosphate of methyl alcohol, 2‐dimethylaminoethanol, 3‐dimethylamino‐1‐propanol and 1,2‐isopropylidene‐ rac ‐glycerol in a “one‐pot procedure” in overall yields of 60–80%. Activation of the reaction with an equimolar mixture of imidazoeland carbon disulfide at the triester formation step permits selective phosphorylation at room temperature. The compounds synthesized represent new triester phospholipid model compounds in which (in addition to glycerol and another requisite alcohol) a steroid and an element other than oxygen are bond to phosphorus.