Efficient synthesis of phospholipids from glycidyl phosphates
2002 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, Vol. 67, no 1, 194-199 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2002. Vol. 67, no 1, 194-199 p.
Engineering and Technology
IdentifiersURN: urn:nbn:se:liu:diva-47127DOI: 10.1021/jo010734+OAI: oai:DiVA.org:liu-47127DiVA: diva2:268023