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O ‐alkyl diol O ‐, S ‐ and Se ‐phosphoroamidates of DL‐α‐tocopherol and their dimethylaminoalkyl derivatives as diester and triester models of phospholipids
Author(s) -
Stamatov Stephan D.,
Gronowitz Salo
Publication year - 1993
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/bf02536322
Subject(s) - chemistry , alkyl , thiophosphate , reagent , ether , medicinal chemistry , organic chemistry , molar ratio , catalysis
Hexamethyltriamide 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 1‐hexadecyloxyethyl‐2‐ O ‐, 1‐hexadecyloxypropyl‐3‐ O ‐, and 1‐hexadecyloxybutyl‐4‐ O ‐(DL‐α‐tocopheryl‐6‐ O )‐( N,N ‐dimethylamido)selenophosphate,‐thiophosphate and‐phosphate derivatives, and some of their 2‐dimethyl‐aminoethyl‐1‐ O ‐, and 3‐dimethylaminopropyl‐1‐ O ‐triester analogues in a “one‐pot procedure” in overall yields of 69–87%. Activation of the reaction with an equimolar mixture of imidazole and carbon disulfide at the triester formation step permits selective phosphorylation at room temperature. The compounds synthesized represent new diester and triester models containing alkyl ether diolphospholipid structures.