Issue 15, 2006
From the journal:

Organic & Biomolecular Chemistry

Tin-mediated synthesis of lyso-phospholipids†

Ezio Fasoli,‡a   Alberto Arnone,a   Antonio Caligiuri,a   Paola D'Arrigo,a   Lorenzo de Ferrab  and  Stefano Servi*a  

* Corresponding authors

a Dipartimento di Chimica, Materiali e Ingegneria Chimica, G. Natta Politecnico di Milano, Via Mancinelli 7, Milano, Italy
E-mail: stefano.servi@polimi.it
Fax: +39 2 23993080
Tel: +39 2 23993047

b Chemi SpA, Patrica (Fr), Italy

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.

Graphical abstract: Tin-mediated synthesis of lyso-phospholipids

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Article information

DOI
https://doi.org/10.1039/B604636C
Article type
Paper
Submitted
30 Mar 2006
Accepted
12 Jun 2006
First published
04 Jul 2006

Org. Biomol. Chem., 2006,4, 2974-2978

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Tin-mediated synthesis of lyso-phospholipids

E. Fasoli, A. Arnone, A. Caligiuri, P. D'Arrigo, L. de Ferra and S. Servi, Org. Biomol. Chem., 2006, 4, 2974 DOI: 10.1039/B604636C

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