One-flask synthesis of unsymmetrical phosphodiesters. Selective amine catalysis of the phosphorylation of primary vs. secondary alcohols

F Ramirez, JF Marecek, H Okazaki

Index: Ramirez,F. et al. Journal of the American Chemical Society, 1976 , vol. 98, # 17 p. 5310 - 5319

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Citation Number: 39

Abstract

Abstract: Two different alcohols, RIOH and R20H, are converted into an unsymmetrical phosphodiester,(R'O)(R20)-P (O) OH, without isolation of intermediates. Alternatively, the two alcohols are converted into a phosphotriester,(R'0)-(R20) P (0) OCH (CH3) COCH3, which is isolated and hydrolyzed to the phosphodiester with or without further purification. The procedures are made possible by the efficient imidazole catalysis of the ...