Selective O-acylation of nucleosides

Details Selective O-acylation of nucleosides Selective O-acylation of nucleosides

2006-09-22

2008-10-21

Lewis, Patrick T (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S018500, C536S025300

Reexamination Certificate

active

07439344

ABSTRACT:
The present invention relates to a one-step process for the selective O-acylation of the hydroxy groups of a nucleoside under basic conditions utilizing DMAP and a carboxylic acid anhydride in aqueous heterogenous solvent mixture.

REFERENCES:
patent: 2006/0040890 (2006-02-01), Martin et al.
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Breiner, R. G., et al. “Synthesis of new nucleosides phosphoraziridines as potential site directed Antineoplastic agents,”J. Med. Chem.(1990) vol. 33(9), pp. 2596-2602.
Giorgi, T. et al. “Supramolecular Helices via Self-Assembly of 8-Oxoguanosines,”J. Am. Chem. Soc.(2003) vol. 125(48), pp. 14741-14749.
Martinez, A.P., et al. The acetylation of 1-(β-D-arabinofuranosyl) cytosine1,J. Med. Chem.(1966) vol. 9(2), p. 268.
Matsuda, A. “A Convenient Method for the Selective Acylation of Guanine Nucleosides,”Synthesis(1986), pp. 385-386.
Ohno, M., et al. “Modulation of adenosine receptor affinity and intrinsic efficacy in adenine nucleosides substituted at the 2-position,”Bioorg Med. Chem(2004) vol. 12, pp. 2995-3007.
Sekine, M. “Selective and rapid O-acylation of hydroxy groups of nucleosides by means of Phase transfer catalysis,”Nat. Prod. Res.(1993) 1(4), pp. 251-256.
Zinni, M. A. et al. “Enzymatic Alcoholysis of 3′,5′-di-O-acetyl-2′-deoxynucleosides,”J. Molecular Cat. B Enzymatic(2004) vol. 29 pp. 129-132.

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