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Selective Synthesis of Phosphate Monoesters by Dehydrative Condensation of Phosphoric Acid and Alcohols Promoted by Nucleophilic Bases Export

by: Akira Sakakura, Akira Sakakura, Mikimoto Katsukawa, Mikimoto Katsukawa, Kazuaki Ishihara, Kazuaki Ishihara

edited by: Org, Org, Web, Web

Organic Letters, Vol. 7, No. 10. (20 April 2005), pp. 1999-2002.

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Phosphate monoesters are synthesized from a mixture of phosphoric acid (1 or 2 equiv) and alcohols (1 equiv) in the presence of tributylamine. The reaction is promoted by nucleophilic bases such as N-alkylimidazole and 4-(N,N-dialkylamino)pyridine. 2',3'-O-Isopropylidene ribonucleosides are selectively converted to their 5'-monophosphates without the protection of amino groups in nucleobases.


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