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Abstract
Reagents for the phosphorylative coupling of two different alcohols are obtained from five-membered cyclic enediolphosphates and acyl phosphates. The primary alcohol of a diol is selectively phosphorylated in the presence of an unprotected secondary alcohol. The acetoinyl group (Ac.Me.CH) is used to block the phosphate function in the synthesis of unsymmetrical phosphodiesters. Phosphomonoesters can also be made by the proper choice of one of the two alcohols. The method has been applied to the synthesis of oligonucleotide models.