title: Tin-mediated synthesis of lyso-phospholipids.
abstract: 1-O-Acyl-sn-glycero-3-phosphocholine and 1-O-acyl-sn-glycero-3-phosphoric acid have been prepared selectively and with high yields from the corresponding diols, glycerophosphoryl choline and glycerol-3-phosphate. Starting from the diols, the activated tin ketals were prepared in 2-propanol by reaction with dialkyltin oxide. The intermediates were acylated in the same solvent with long-chain fatty acid chlorides, giving the corresponding 1-acyl-lyso-phospholipids in high yield and with complete regioselectivity. The catalytic nature of the tin-mediated acylation and the relevance of the solvent are discussed.
authors.affiliation: Dipartimento di Chimica, Materiali e Ingegneria Chimica, G. Natta Politecnico di Milano, Italy.
authors.forename: Ezio
authors.initials: E
authors.lastname: Fasoli
authors.forename: Alberto
authors.initials: A
authors.lastname: Arnone
authors.forename: Antonio
authors.initials: A
authors.lastname: Caligiuri
authors.forename: Paola
authors.initials: P
authors.lastname: D'Arrigo
authors.forename: Lorenzo
authors.initials: L
authors.lastname: de Ferra
authors.forename: Stefano
authors.initials: S
authors.lastname: Servi