Regiospecific and highly stereoselective coupling of 6-(substituted- imidazol-1-yl)purines with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro- pentofuranosyl chloride. Sodium-salt glycosylation in binary solvent mixtures: Improved synthesis of cladribine

Journal of Organic Chemistry

Volumn 71, Issue 20, 2006, Pages 7773-7779

  Zhong, Minghong ^a   Nowak, Ireneusz ^a   Robins, Morris J ^a  

^a Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; BINARY MIXTURES; ISOMERS; ORGANIC SOLVENTS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AMMONOLYSIS; ANOMERIZATION; ANTICANCER DRUGS; NONPOLAR SOLVENTS;

NITROGEN COMPOUNDS;

2 CHLORO 6 (IMIDAZOL 1 YL)PURINE DERIVATIVE; 2 DEOXY 3,5 DI O (4 TOLUOYL) ALPHA DEXTRO ERYTHROPENTOFURANOSYL CHLORIDE; 2' DEOXYNUCLEOSIDE; 6 (IMIDAZOL 1 YL)PURINE DERIVATIVE; ACETONITRILE; CARBOHYDRATE DERIVATIVE; CLADRIBINE; FURAN DERIVATIVE; IMIDAZOLE DERIVATIVE; PURINE DERIVATIVE; SODIUM DERIVATIVE; UNCLASSIFIED DRUG;

AMMONOLYSIS; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; REACTION ANALYSIS; SOLUBILITY; SOLVATION; STEREOCHEMISTRY;

ANTINEOPLASTIC AGENTS; CARBOHYDRATES; CLADRIBINE; GLYCOSYLATION; PURINES; SOLVENTS; STEREOISOMERISM;

EID: 33749129770     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061282+     Document Type: Article

References (49)

1. (a) Nucleic Acid Related Compounds. 137. For Paper 136 see: Lin, X.; Robins, M. J. Collect. Czech. Chem. Commun., in press.
2. (b) Patent application filed.
3. (a) Robins, M. J.; Robins, R. K. J. Am. Chem. Soc. 1965, 87, 4934-4940.
4. (b) Christensen, L. F.; Broom, A. D.; Robins, M. J.; Bloch, A. J. Med. Chem. 1972, 15, 735-739.
5. (a) Piro, L. D.; Carrera, C. J.; Carson, D. A.; Beutler, E. N. Engl. J. Med. 1990, 322, 1117-1121.
6. (b) Jehn, U.; Bartl, R.; Dietzfelbinger, H.; Vehling-Kaiser, U.; Wolf-Hornung, B.; Hill, W.; Heinemann, V. Ann. Hematol. 1999, 78, 139-144.
7. Bryson, H. M.; Sorkin, E. M. Drugs 1993, 46, 872-894.
8. Santana, V. M.; Mirro, J., Jr.; Kearns, C.; Schell, M. J.; Crom, W.; Blakley, R. L. J. Clin. Oncol. 1992, 10, 364-370.
9. Piro, L. D.; Carrera, C. J.; Beutler, E.; Carson, D. A. Blood 1988, 72, 1069-1073.
10. Kong, L. R.; Samuelson, E.; Rosen, S. T.; Roenigk, H. H., Jr.; Tallman, M. S.; Rademaker, A. W.; Kuzel, T. M. Leuk. Lymphoma 1997, 26, 89-97.
11. Robak, T.; Gora-Tybor, J.; Krykowski, E.; Walewski, J. A.; Borawska, A.; Pluzanska, A.; Potemski, P.; Hellmann, A.; Zaucha, J. M.; Konopka, L.; Ceglarek, B.; Durzynski, T.; Sikorska, A.; Michalak, K.; Urasinski, J.; Opalinska, J.; Dmoszynska, A.; Adamczyk-Cioch, M. B.; Kuratowska, Z.; Dwilewicz-Trojaczek, J.; Boguradzki, P.; Deren, M.; Maj, S.; Grieb, P. Leuk. Lymphoma 1997, 26, 99-105.
12. Beutler, E.; Sipe, J. C.; Romine, J. S.; Koziol, J. A.; McMillan, R.; Zyroff, J. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 1716-1720.
13. Chen, R. H. K. U.S. Patent 5,208,327, 1993; Chem. Abst. 1993, 119, 160729.
14. Janeba, Z.; Francom, P.; Robins, M. J. J. Org. Chem. 2003, 68, 989-992.
15. (a) Mikhailopulo, I. A.; Zinchenko, A. I.; Kazimierczuk, Z.; Barai, V. N.; Bokut, S. B.; Kalinichenko, E. N. Nucleosides Nucleotides 1993, 12, 417-422.
16. (b) Barai, V. N.; Zinchenko, A. I.; Eroshevskaya, L. A.; Kalinichenko, E. N.; Kulak, T. I.; Mikhailopulo, I. A. Helv. Chim. Acta 2002, 85, 1901-1908.
17. Venner, H. Chem. Ber. 1960, 93, 140-149.
18. (a) Ikehara, M.; Tada, H. J. Am. Chem. Soc. 1963, 85, 2344-2345.
19. (b) Ikehara, M.; Tada, H. J. Am. Chem. Soc. 1965, 87, 606-610.
20. (a) Kazimierczuk, Z.; Cottam, H. B.; Revankar, G. R.; Robins, R. K. J. Am. Chem. Soc. 1984, 106, 6379-6382.
21. (b) Robins, R. K.; Revankar, G. R. Eur. Pat. Appl. 173,059, 1986; Chem. Abst. 1986, 105, 60911u.
22. Hildebrand, C.; Wright, G. E. J. Org. Chem. 1992, 57, 1808-1813.
23. Gupta, P. K.; Munk, S. A. U.S. Pat. Appl. 2004/039190, 2004; Chem. Abst. 2004, 140, 199639.
24. Kazimierczuk, Z.; Kaminski, J. Polish Patent 177,960, 2000; Chem. Abst. 2001, 134, 208061.
25. Gerszberg, S.; Alonso, D. PCT Int. Appl. 2000064918, 2000; Chem. Abst. 2000, 133, 310116.
26. Zhong, M.; Nowak, I.; Cannon, J. F.; Robins, M. J. J. Org. Chem. 2006, 71, 4216-4221.
27. Zhong, M.; Nowak, I.; Robins, M. J. Org. Lett. 2005, 7, 4601-4603.
28. (a) Hoffer, M. Chem. Ber. 1960, 93, 2777-2781.
29. (b) Rolland, V.; Kotera, M.; Lhomme, J. Synth. Commun. 1997, 27, 3505-3511.
30. Hubbard, A. J.; Jones, A. S.; Walker, R. T. Nucleic Acids Res. 1984, 12, 6827-6837.
31. Kawakami, H.; Matsushita, H.; Naoi, Y.; Itoh, K.; Yoshikoshi, H. Chem. Lett. 1989, 235-238.
32. Ugarkar, B. G.; Castellino, A. J.; DaRe, J. M.; Kopcho, J. J.; Wiesner, J. B.; Schanzer, J. M.; Erion, M. D. J. Med. Chem. 2000, 43, 2894-2905.
33. (a) Khajehpour, M.; Kauffman, J. F. J. Phys. Chem. A 2000, 104, 7151-7159.
34. (b) Khajehpour, M.; Welch, C. M.; Kleiner, K. A.; Kauffman, J. F. J. Phys. Chem. A 2001, 105, 5372-5379.
35. (c) Marcus, Y. Solvent Mixtures; Marcel Dekker: New York, 2002.
36. (d) Wu, Y. G.; Tabata, M.; Takamuku, T. J. Solution Chem. 2002, 31, 381-395.
37. Wilson, G. M. J. Am. Chem. Soc. 1964, 86, 127-130.
38. Deng, D.; Li, H.; Yao, J.; Han, S. Chem. Phys. Lett. 2003, 376, 125-129.
39. Jaworski, J. S. J. Phys. Org. Chem. 2002, 15, 319-323.
40. (a) Zhong, M.; Han, B.; Van, H. J. Supercrit. Fluids 1997, 10, 113-118.
41. (b) Zhong, M.; Han, B.; Van, H.; Peng, D.-Y. Fluid Phase Equilib. 1997, 134, 175-183.
42. CRC Handbook of Chemistry and Physics, 86th ed.; Lide, D. R., Ed.; Taylor & Francis: Boca Raton, 2005-2006; pp 8-127.
43. (a) Abraham, M. H.; Taft, R. W.; Kamlet, M. J. J. Org. Chem. 1981, 46, 3053-3056.
44. (b) Taft, R. W.; Abboud, J.-L. M.; Kamlet, M. J.; Abraham, M. H. J. Solution Chem. 1985, 14, 153-186.
45. Zhong, M. Ph.D. Dissertation, Brigham Young University, 2004.
46. Bauta, W. E.; Schulmeier, B. E.; Burke, B.; Puente, J. F.; Cantrell, W. R., Jr.; Lovett, D.; Goebel, J.; Anderson, B.; Ionescu, D.; Guo, R. Org. Process Res. Dev. 2004, 8, 889-896.
47. Schaeffer, H. J.; Thomas, H. J. J. Am. Chem. Soc. 1958, 80, 3738-3742.
48. Zhong, M.; Strobel, S. A. Org. Lett. 2006, 8, 55-58.
49. General experimental items are in Supporting Information.