Aryl H-phosphonates. 14. Synthesis of new nucleotide analogues with phosphonate-phosphate internucleosidic linkage

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3571-3573

  Szymczak, Marzena ^a   Szymańska, Agnieszka ^a   Stawiński, Jacek ^a,b   Boryski, Jerzy ^a   Kraszewski, Adam ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Poland)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE; NUCLEOTIDE; ORGANOPHOSPHATE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

NUCLEOSIDES; NUCLEOTIDES; PHOSPHONIC ACIDS; PHOSPHORIC ACID ESTERS;

EID: 0142106446     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035166u     Document Type: Article

References (20)

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13. Compounds 2 were obtained by modification of the method of van Boom et al. (de Vroom, E.; Spierenburg, M. L.; Dreef, C. E.; Van der Marel, G. A.; Van Boom, J. H. Recl. Trav. Chim. Pays-Bas 1987, 106, 65-66) that involved acylation of a nucleoside bis(trimethylsilyl)phosphite with respective acyl chloride.
14. 31P NMR spectra) and the observed chemical reactivity.
15. 31P NMR spectra.
16. 31P NMR spectroscopy, probably the rate determining step in this process is the formation of the hydroxyphosphonate derivative. More detail studies on this are currently being carried out in our laboratory.
17. The identity of compounds 8 and 9 was confirmed by comparison with authentic samples obtained in other ways. (a) Cieślak, J.; Jankowska, J. ; Sobkowski, M.; Wenska, M.; Stawiński, J.; Kraszewski, A. J. Chem. Soc., Perkin Trans. 1 2002, 31-37. (b) Jankowska, J.; Sobkowski, M.; Stawiński, J.; Kraszewski, A. Tetrahedron Lett. 1994, 35, 3355-3358.
18. The identity of compounds 8 and 9 was confirmed by comparison with authentic samples obtained in other ways. (a) Cieślak, J.; Jankowska, J. ; Sobkowski, M.; Wenska, M.; Stawiński, J.; Kraszewski, A. J. Chem. Soc., Perkin Trans. 1 2002, 31-37. (b) Jankowska, J.; Sobkowski, M.; Stawiński, J.; Kraszewski, A. Tetrahedron Lett. 1994, 35, 3355-3358.
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20. 3 95:5 (v/v) and applied to a silica gel column equilibrated with the same solvent. Compounds 7a-c were isolated by using a linear gradient of water [0-10% (v/v)] in propanol-2/conc NH3 95:5 (v/v). Fractions containing pure compounds were collected and evaporated with an added excess of propanol-2 to afford products 7a-c (ammonium salts) as amorphous white powder.