An improved synthesis of 9-[2-(diethoxyphosphonomethoxy)ethyl]adenine and its analogues with other purine bases utilizing the Mitsunobu reaction

Nucleosides and Nucleotides

Volumn 15, Issue 11-12, 1996, Pages 1771-1778

  Chen, Wei ^a   Flavin, Michael T ^a   Filler, Robert ^b   Xu, Ze Qi ^a  

^a MediChem Research Inc   (United States)

^b ILLINOIS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIAMINOPURINE; 9 [2 (DIETHOXYPHOSPHONOMETHOXY)ETHYL]ADENINE; ADENINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; COUPLING FACTOR; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS; HYDROLYSIS; NONHUMAN; PURINE METABOLISM; REACTION ANALYSIS; SPECTROSCOPY;

HERPES; SIMPLEXVIRUS;

EID: 0029955075     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319608002731     Document Type: Article

References (16)

1. Hughes, D. L. Org. React. 1992, 42, 335-656.
2. Jenny, T. F.; Previsani, N.; Benner, S. A. Tetrahedron Lett. 1991, 32, 7029-7032.
3. Bonnal, C.; Chavis, C.; Lucas, M. J. Chem. Soc. Perkin Trans, 1 1994, 1401-1410.
4. Overberger, C. G.; Chang, J. Y. Tetrahedron Lett. 1989, 30, 51-54.
5. De Clercq, E.; Holy, A.; Rosenberg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P. C. Nature 1986, 323, 464-467.
6. De Clercq, E.; Sakuma, T.; Baba, M.; Pauwels, R.; Balzarini, J.; Rosenberg, I.; Holy, A. Antiviral Res. 1987, 8, 261-272.
7. Heijtink, R. A.; Kruining, J.; De Wilde, G. A.; Balzarini, J.; De Clercq, E.; Schalm, S. W. Antimicrob. Agents Chemother. 1994, 58, 2180-2182.
8. Pauwels, R.; Balzarini, J.; Schols, D.; Baba, M.; Desmyter, J.; Rosenberg, I.; Holy, A.; De Clercq, E. Antimicrob. Agents Chemother. 1988, 32, 1025-1030.
9. Balzarini, J.; Naesens, L.; Herdewijn, P.; Rosenberg, I.; Holy, A.; Pauwels, R.; Baba, M.; Jones, D. G.; De Clercq, E. Proc. Natl. Acad. Sci. USA 1989, 86, 332-336.
10. Gong, Y.-F.; Marshall, D. R.; Srinivas, R. V.; Fridland, A. Antimicrob. Agents Chemother. 1994, 38, 1683-1687.
11. Holy, A.; Rosenberg, I. Collect. Czech. Chem. Commun. 1987, 52, 2801-2809.
12. Holy, A.; De Clercq, E.; Votruba, I. In Nucleotide Analogues as Antiviral Agents; Martin, J. C. Ed.; ACS Washington, D. C., 1989; Chapter 4, pp 51-71.
13. Bronson, J. J.; Kim, C. U.; Ghazzouli, I.; Hitchcock, M. J. M.; Kern, E. R.; Martin, J. C. see ref. 12, Chapter 5, pp 72-87.
14. Bailey, W. F.; Zarcone, L. M.; Rivera, A. D. J. Org. Chem. 1995, 60, 2532-2536.
15. 2 for synthesis of 4 has been reported in a patent: Webb, R. R., Jr., et al. European Patent Publication 0269947B1, 1992.
16. Arbuzov, B. A.; Ukhvatova, E. N. Zh. Obshch. Khim. 1959, 29, 503-507.