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Glyceroamidothiophosphates of cholecalciferol (Vitamin D 3 )
Author(s) -
Stamatov Stephan D.,
Gronowitz Salo
Publication year - 1990
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/bf02544329
Subject(s) - glycerol , reagent , thiophosphate , chemistry , lipidology , cholecalciferol , molar ratio , monoglyceride , medicinal chemistry , organic chemistry , vitamin , biochemistry , catalysis , clinical chemistry , fatty acid
The hexamethyltriamide of phosphorous acid activated by the addition of iodine at the optimum molar ratio 1.05∶0.05 was used as a phosphorylating reagent to synthesize cholecalciferyl‐3‐ 0 ‐( N,N ‐dimethylamido)thiophosphate derivatives of 1,3‐benzylidene‐ rac ‐glycerol, 1,2‐isopropylidene‐ rac ‐glycerol, 1,3‐dioleoyl‐ rac ‐glycerol, and 1,2‐dioleoyl‐ rac ‐glycerol in a one‐pot procedure in high overall yields (81–86%). The compounds represent new model types of phospholipid structures which, in addition to glycerol and a steroid fragment, contain a biologically important linkage other than an oxygen‐phosphorus bond.