52603-03-9Relevant academic research and scientific papers
Efficient synthesis of phospholipids from glycidyl phosphates
Lindberg, Jan,Ekeroth, Johan,Konradsson, Peter
, p. 194 - 199 (2007/10/03)
New efficient routes to enantiopure phospholipids, starting from (S)-glycidol, are described. Lysophosphatidic acids and phosphatidic acids were obtained in good overall yields from (S)-glycidol, in only three and four steps, respectively. Moreover, the strategy can also be used to produce phosphatidylcholines in three steps. Using dialkylphosphoramidites, (S)-glycidol was phosphorylated to give (R)-1-O-glycidyl dialkyl phosphates. Regiospecific epoxide opening, using hexadecanol or cesium palmitate, followed by phosphate deprotection, provided lysophosphatidic acids. 2-O-Esterification prior to phosphate deprotection provided 1,2-O-diacyl and 1-O-alkyl-2-O-acyl phosphatidic acids. Phosphorylation of (S)-glycidol using phosphorus oxychloride followed by in situ treatment with choline tosylate produced (R)-glycidyl phosphocholine. Subsequent nucleophilic opening of the epoxide using cesium palmitate produced 1-O palmitoyl-sn-glycero-3-phosphocholine, which has been used in syntheses of phosphatidylcholines.
Synthesis and chemical transformations of 4-hexadecyloxymethyl-2-oxo-2-chloro-1,3,2-dioxaphospholane
Malekin,Khromova,Kisin,Kruglyak,Kurochkin
, p. 677 - 682 (2007/10/03)
Cyclophosphorylation of 1-hexadecylglycerol with phosphorus oxychloride afforded 4-hexadecyl-oxymethyl-2-oxo-2-chloro-1,3,2-dioxaphospholane (I) with high yield. By means of 1H, 13C, and 31P NMR, it was shown to be a 1 : 9 mixture of two stable epimers with equatorial and axial configuration of the chlorine atom, respectively. Phospholane (I) entered into nucleophilic reactions with KHCO3 and HN(Pri)2 to give 80-85% yields of the chlorine substitution products with the phospholane cycle remaining intact. Interaction of the phospholane (I) with water or choline tosylate also initially produced substituted phospholanes, as shown by NMR. Subsequent hydrolysis led to the cleavage of the phospholane ring and to formation of isomeric 1-hexadecylglycero-2- and 3-phosphates and 1-hexadecylglycero-2- and 3-phosphocholines, respectively. A method for the separation of isomeric phosphates was developed, which made it possible to isolate 1-hexadecylglycero-2-phosphate and 1-hexadecylglycero-3-phosphate.
