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

作者：Ioannou Panayiotis V^*; Tsivgoulis Gerasimos M

来源：Chemistry and Physics of Lipids, 2010, 163(1): 51-55.

DOI：10.1016/j.chemphyslip.2009.10.008

• Arsonolipids
• 2,3-Diacyloxypropylarsonic acids
• Fatty acyl chlorides
• Fatty acid anhydrides
• Boron trifluoride etherate

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 similar to 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 RCOCI and BF(3)-Et(2)O gave only moderate yields (25-60%) of arsonolipids.

• 出版日期2010-1