A high yield procedure for the preparation of arsonolipids (2,3-diacyloxypropylarsonic acids)

The crucial step in the preparation of the title arsonolipids starting from the dichloromethane-soluble dithioarsonite CH2(OH)CH(OH)CH2-As(SPh)2 is to avoid an internal cyclization during the acylation which protects the primary -OH group from being acylated. This was to a large extent accomplished by using fatty acyl chloride in the presence of the weak base pyridine and controlling the temperature and rate of the acyl chloride addition, giving ∼70% yields of arsonolipids. The presence of catalytic amounts of 4-dimethylaminopyridine boosted the yields to 82-85%. This yield is a great improvement over the yields (20-55%) previously achieved. The acylating systems (RCO)2O or RCOCl and BF3·Et2O gave only moderate yields (25-60%) of arsonolipids.