Tin-mediated synthesis of lyso-phospholipids.
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.
Fasoli
Ezio
E
Dipartimento di Chimica, Materiali e Ingegneria Chimica, G. Natta Politecnico di Milano, Italy.
Arnone
Alberto
A
Caligiuri
Antonio
A
D'Arrigo
Paola
P
de Ferra
Lorenzo
L
Servi
Stefano
S