Preparation of Pseudo-Arsonolipids: Dl-2,3-Diacyloxybutane-1,4-Bis(Arsonic Acids)

Abstract

The title pseudo-arsonolipid with palmitoyl side chain has been prepared in ∼70% yield from its parent DL-2,3-dihydroxybutane-1,4-bis(arsonic acid) after reduction of the As(V) to As(III) by thiophenol, acylation with palmitoyl chloride in the presence of pyridine and catalytic amounts of 4-(dimethylamino)pyridine, and reoxidation of As(III) to As(V) by hydrogen peroxide. In CDCl₃/CD₃OD esterification of the –AsO₃H₂ groups was detected by ¹H NMR.

GRAPHICAL ABSTRACT

Keywords:

• Pseudo-arsonolipids
• 2,3-dihydroxybutane-1,4-bis(arsonic acids)
• DL-2,3-diacyloxybutane-1,4-bis(arsonic acids)
• acylation

Acknowledgments

We thank Dr G. M. Tsivgoulis for simulating the spectrum of DL-11 to establish the ABX pattern.