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Chemistry and physics of lipids

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


PMID 19900427

Abstract

The crucial step in the preparation of the title arsonolipids starting from the dichloromethane-soluble dithioarsonite CH(2)(OH)CH(OH)CH(2)-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 approximately 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)(2)O or RCOCl and BF(3).Et(2)O gave only moderate yields (25-60%) of arsonolipids.