Synthesis of 5′-amino-5′-phosphonate analogues of pyrimidine nucleoside monophosphates

Journal of Organic Chemistry

Volumn 68, Issue 16, 2003, Pages 6108-6114

  Chen, Xuemei ^a   Wiemer, David F ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SINGLE CRYSTAL DIFFRACTION;

BENZENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHATES; SINGLE CRYSTALS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALDEHYDES;

CYTARABINE; CYTIDINE; CYTIDINE 5' AMINO 5' PHOSPHONATE DERIVATIVE; DRUG ANALOG; PYRIMIDINE NUCLEOSIDE DERIVATIVE; PYRIMIDINE NUCLEOSIDE MONOPHOSPHATE DERIVATIVE; UNCLASSIFIED DRUG; URIDINE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PHOSPHONIC ACID DERIVATIVE; PYRIMIDINE NUCLEOSIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DIFFRACTION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

CHROMATOGRAPHY, THIN LAYER; CYTARABINE; CYTIDINE; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; PHOSPHONIC ACIDS; PYRIMIDINE NUCLEOSIDES; STEREOISOMERISM; URIDINE;

EID: 0042031240     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030050x     Document Type: Article

References (32)

1. Grant, S. Adv. Cancer Res, 1998, 72, 197-233.
2. Chen, X.; Wiemer, A. J.; Hohl, R. J.; Wiemer, D. F. J. Org. Chem. 2002, 67, 9331-9339.
3. (a) Yager, K. M.; Taylor, C. M.; Smith, A. B., III. J. Am. Chem. Soc. 1994, 116, 9377-9378.
4. (b) Smith, A. B., III; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1995, 117, 10879-10888.
5. (a) Atherton, F. R.; Hassall, C. H.; Lambert, R. W. J. Med. Chem. 1986, 29, 29-40.
6. (b) Mcleod, D. A.; Brinkworth, R. I.; Ashley, J. A.; Janda, K. D.; Wirsching, P. Bioorg. Med. Chem. Lett. 1991, 1, 653-658.
7. (c) Hirschmann, R.; Smith, A. B., III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Benkovic, S. J. Science 1994, 265, 234-237.
8. Groger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103.
9. De Risi, C.; Dondoni, A.; Perrone, D.; Pollini, G. P. Tetrahedron Lett. 2001, 42, 3033-3036.
10. (a) Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465-6468.
11. (b) Song, Y.; Niederer, D.; Lane-Bell, P. M.; Lam, L. K. P.; Crawley, S.; Palcic, M. M.; Pickard, M. A.; Pruess, D. L.; Vederas, J. C. J. Org. Chem. 1994, 59, 5784-5793.
12. Hammerschmidt, F.; Wuggenig, F. Tetrahedron: Asymmetry. 1999, 10, 1709-1721.
13. Hammerschmidt, F.; Hanbauer, M. J. Org. Chem. 2000, 65, 6121-6131.
14. (a) Boehm, J. C.; Kingsbury, W. D. J. Org. Chem. 1986, 51, 2307-2314.
15. (b) Masson, G.; Compain, P.; Martin, O. Org. Lett. 2000, 2, 2971-2974.
16. (c) Feldman, K. S.; Mingo, P. A.; Hawkins, P. C. D. Heterocycles 1999, 51, 1283-1293.
17. (a) Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021-3028.
18. (b) Johansson R.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1984, 2371-2374.
19. (a) Yoshimura, J.; Yamaura, M.; Suzuki, T.; Hashimoto, H. Chem. Lett. 1983, 1001-1002.
20. (b) Yamaura, M.; Suzuki, T.; Hashimoto, H.; Yoshimura, J.; Okamoto, T.; Shin, C. Bull. Chem. Soc. Jpn. 1985, 58, 1413-1420.
21. (a) Singh, S. B. Tetrahedron Lett. 1995, 36, 2009-2012.
22. (b) Bull, S. D.; Davies, S. G.; Fenton, G.; Mulvaney, A. W.; Prasad, R. S.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2000, 3765-3774.
23. (a) Pierce, M. E.; Parsons, R. L, Jr.; Radesca, L. A.; Lo, Y. S.; Silverman, S.; Moore, J. R.; Islam, Q.; Choudhury, A.; Fortunak, J. M. D.; Nguyen, D. Luo, C.; Morgan, S. J.; Davis, W. P.; Confalone, P. N.; Chen, C. Y.; Tillyer, R. D.; Frey, L.; Tan, L.; Xu, F.; Zhao, D.; Thompson, A. S.; Corley, E. G.; Grabowski, E. J. J.; Reamer, R.; Reider, P. J. J. Org. Chem. 1998, 63, 3, 8536-8543.
24. (b) Gunji, H.; Vasella, A. Helv. Chim. Acta 2000, 83, 3229-3245.
25. (c) Adams, H.; Anderson, J. C.; Peace, S.; Pennell, A. M. K. J. Org. Chem. 1998, 63, 9932-9934.
26. (a) McEldoon, W. L.; Wiemer, D. F. Tetrahedron 1995, 51, 7131-7148.
27. (b) Lefebvre, I. M.; Evans, S. A., Jr. J. Org. Chem. 1997, 62, 7532-7533.
28. (c) Davis, F. A.; Lee, S.; Yan, H.; Titus, D. D. Org. Lett. 2001, 3, 1757-1760.
29. Zhu, X. F.; Williams, H. J.; Scott, A. I. J. Chem. Soc., Perkin Trans. 1 2000, 2305-2306.
30. Bubenik, M.; Rej, R.; Nguyen-Ba, N.; Attardo, G.; Ouellet, F.; Chan, L. Bioorg. Med. Chem. Lett. 2002, 12, 3063-3066.
31. The single-crystal X-ray diffraction data for compound 15 is available from Cambridge Crystallographic Data Centre with reference number CCDC 197774.
32. Hruska, F. E.; Blonski, W. J. P. Can. J. Chem. 1982, 60, 3026-3032.