Palmitoyl diol S- and O-phosphoroamidates of some sterols.
The hexamethylphosphorus triamide activated by the addition of iodine at the optimum molar ratio 1.05:0.05 was used as a phosphorylating reagent to synthesize 1-palmitoyloxyethyl-2-O-, 1-palmitoyloxypropyl-3-O- and 1-palmitoyloxybutyl-4-O-(N,N-dimethylamido)thiophosphate and -phosphate derivatives of beta-sitosterol, cholesterol and stigmasterol in a one-pot procedure with overall yields of 80-87%. 1-Palmitoyloxypropyl-3-O-(cholesteryl-3-O)-(N,N-dimethylamido++ +) phosphite was used as a model synthon for the preparation of transamidated morpholido-thiophosphate and -phosphate analogues with final yields of 82-86%.
Stamatov
S D
SD
Department of Organic Chemical Technology, University of Plovdiv, Bulgaria.
Staneva
V K
VK
D000577:Amides / Q000138:chemical synthesis*; D008956:Models, Chemical; D015394:Molecular Structure; D010169:Palmitic Acids / Q000138:chemical synthesis*; D010743:Phospholipids / Q000737:chemistry*; D010766:Phosphorylation; D013261:Sterols / Q000737:chemistry*
D000577:Amides; D010169:Palmitic Acids; D010743:Phospholipids; D013261:Sterols