title: Palmitoyl diol S- and O-phosphoroamidates of some sterols.
abstract: 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%.
authors.affiliation: Department of Organic Chemical Technology, University of Plovdiv, Bulgaria.
authors.forename: S D
authors.initials: SD
authors.lastname: Stamatov
authors.forename: V K
authors.initials: VK
authors.lastname: Staneva
mesh_terms: 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*
chemical_list: D000577:Amides; D010169:Palmitic Acids; D010743:Phospholipids; D013261:Sterols