Synthesis and reactions of 2-chloro- and 2-tosyloxy-2′-deoxyinosine derivatives

Journal of Organic Chemistry

Volumn 70, Issue 18, 2005, Pages 7188-7195

  Pottabathini, Narender ^a   Bae, Suyeal ^a,b   Pradhan, Padmanava ^a   Hahn, Hoh Gyu ^b   Mah, Heduck ^c   Lakshman, Mahesh K ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b Korea Institute of Science and Technology   (South Korea)

^c Kyonggi University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ETHERS; PALLADIUM; SYNTHESIS (CHEMICAL);

2-CHLORO- AND 2-TOSYLOXY-2′-DEOXYINOSINE; C-C CROSS-COUPLINGS; ELECTROPHILIC NUCLEOSIDES; GLYCOSYLATION TECHNIQUES;

DERIVATIVES;

2 CHLORO 2' DEOXYINOSINE DERIVATIVE; 2 TOSYLOXY 2' DEOXYINOSINE DERIVATIVE; ALLYL COMPOUND; BROMINE DERIVATIVE; CARBON; CHLORINE DERIVATIVE; DEOXYGUANOSINE; DEOXYINOSINE; FLUORINE DERIVATIVE; NUCLEOSIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILANE DERIVATIVE; TERT BUTYLDIMETHYLSILYL ETHER DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; COMPARATIVE STUDY; CROSS COUPLING REACTION; ELECTRON; GLYCOSYLATION; HALOGENATION; ISOMERISM; SYNTHESIS;

DEOXYGUANOSINE; INOSINE;

EID: 24144448736     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050847j     Document Type: Article

References (54)

1. For some examples, please see: (a) Srivastava, P. C.; Robins, R. K.; Meyer, R. B., Jr. In Chemistry of Nucleosides and Nucleotides: Townsend, L. B., Ed.; Plenum Press: New York, 1988; Chapter 2, pp 113-280.
2. (b) Robins M. J.; Uznański B. Can. J. Chem. 1981, 59, 2601-2607.
3. (c) Trivedi, B. K. Nucleosides Nucleotides 1988, 7, 393-402.
4. (d) Trivedi, B. K.; Bruns, R. F. J. Med. Chem. 1989, 32, 1667-1673.
5. (e) Cosstick, R.; Douglas, M. E. J. Chem. Soc., Perkin Trans. 1 1991, 1035-1040.
6. (f) van der Wenden, E. M.; von Frijtag Drabbe Künzel, J. K.; Mathôt, R. A. A.; Danhof, M.; IJzerman, A. P.; Soudijn, W. J. Med. Chem. 1995, 38, 4000-4006.
7. (g) Robins, M. J.; Basom, G. L. Can. J. Chem. 1973, 51, 3161-3169.
8. (h) Lakshman, M.; Lehr, R. E. Tetrahedron Lett. 1990, 31, 1547-1550.
9. (i) Chaturvedi, S.; Lakshman, M. K. Carcinogenesis 1996, 17, 2747-2752.
10. (j) Kim, S. J.; Jajoo, H. K.; Kim, H.-Y.; Zhou, L.; Horton, P.; Harris, C. M.; Harris, T. M. Bioorg. Med. Chem. 1995, 3, 811-822.
11. (k) Ferentz, A. E.; Verdine, G. L. Nucleosides Nucleotides 1992, 11, 1749-1763.
12. (l) Gao, H.; Fathi, R.; Gaffney, B. L.; Goswami, B.; Kung, P.-P.; Rhee, Y.; Jin, R.; Jones, R. A. J. Org. Chem. 1992, 57, 6954-6959.
13. (m) Samano, V.; Miles, R. W.; Robins, M. J. J. Am. Chem. Soc. 1994, 116, 9331-9332.
14. (n) Gerster, J. F.; Robins, R. K. J. Am. Chem. Soc. 1965, 87, 3752-3759.
15. De Riccardis, F.; Johnson, F. Org. Lett. 2000, 2, 293-295.
16. Robins, M. J.; Robins, R. K. J. Org. Chem. 1969, 34, 2160-2163.
17. Jhingan, A. K.; Meehan, T. Synth. Commun. 1992, 22, 3129-3135.
18. Robins, M. J.; Uznanski, B. Can. J. Chem. 1981, 59, 2608-2611.
19. (a) Lee, H.; Hinz, M.; Stezowski, J. J.; Harvey, R. G. Tetrahedron Lett. 1990, 31, 6773-6776.
20. (b) Woo, J.; Sigurdsson, S. T.; Hopkins, P. B. J. Am. Chem. Soc. 1993, 115, 3407-3415.
21. (a) Harris, C. M.; Zhou, L.; Strand, E. A.; Harris, T. M. J. Am. Chem. Soc. 1991, 113, 4328-4329.
22. (b) Zajc, B. Lakshman, M. K.; Sayer, J. M.; Jerina, D. M. Tetrahedron Lett. 1992, 33, 3409-3412.
23. Harwood, E. A.; Sigurdsson, S. T.; Edfeldt, N. B. F.; Reid, B. R.; Hopkins, P. B. J. Am. Chem. Soc. 1999, 121, 5081-5082.
24. (a) Cook, P. D.; Ramasamy, K. S.; Manoharan, M. U.S. Pat. 5459255, 1995.
25. (b) Miraglia, L. J.; Nero, P.; Graham, M. J.; Monia, B. P.; Koller, E.; Chiang, M. Y.; Manoharan, M. U.S. Pat. Appl. Publ. 20030203862, 2003.
26. Ramasamy, K. S.; Bakir, F.; Baker, B.; Cook, P. D. J. Heterocycl. Chem. 1993, 30, 1373-1377.
27. Ramasamy, K. S.; Zounes, M.; Gonzalez, C.; Freier, S. M.; Lesnik, E. A.; Cummins, L. L.; Griffey, R. H.; Monia, B. P.; Cook, P. D. Tetrahedron Lett. 1994, 35, 215-218.
28. Manoharan, M.; Ramasamy, K. S.; Mohan, V.; Cook, P. D. Tetrahedron Lett. 1996, 37, 7675-7678.
29. Kazimierczuk, Z.; Cottam, H. B.; Revankar, G. R.; Robins, R. K. J. Am. Chem. Soc. 1984, 106, 6379-6382.
30. Hoffer, M. Chem. Ber. 1960, 93, 2777-2781.
31. (a) Steinbrecher, T.; Wameling, C.; Oesch, F.; Seidel, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 404-406.
32. (b) Edwards, C.; Boche, G.; Steinbrecher, T.; Scheer, S. J. Chem. Soc., Perkin Trans. 1 1997, 1887-1893.
33. Cooper, M. D.; Hodge, R. P.; Tamura, P. J.; Wilkinson, A. S.; Harris, C. M.; Harris, T. M. Tetrahedron Lett. 2000, 41, 3555-3558.
34. For our recent reviews, please see: (a) Lakshman, M. K. J. Organomet. Chem. 2002, 653, 234-251.
35. (b) Lakshman, M. K. Curr. Org. Synth. 2005, 2, 83-112.
36. Lakshman, M. K.; Ngassa, F. N.; Keeler, J. C.; Dinh, Y. Q. V.; Hilmer, J. H.; Russon, L. M. Org. Lett. 2000, 2, 927-930.
37. Francom, P.; Janeba, Z.; Shibuya, S.; Robins, M. J. J. Org. Chem. 2002, 67, 6788-6796.
38. Francom, P.; Robins, M. J. J. Org. Chem. 2003, 65, 666-669.
39. + + H): 605.2746, found 605.2774.
40. (a) Nair, V.; Turner, G. A.; Chamberlain, S. D. J. Am. Chem. Soc. 1987, 109, 7223-7224.
41. (b) Nair, V.; Turner, G. A.; Buenger, G. S.; Chamberlain, S. D. J. Org. Chem. 1988, 53, 3051-3057.
42. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley-Interscience: New York, 1999; pp 68-74.
43. Lakshman, M. K.; Hilmer, J. H.; Martin, J. Q.; Keeler, J. C.; Dinh, Y. Q. V.; Ngassa, F. N.; Russon, L. M. J. Am. Chem. Soc. 2001, 123, 7779-7787.
44. Hayakawa, Y.; Kato, H.; Uchiyama, M.; Kajino, H.; Noyori, R. J. Org. Chem. 1986, 51, 2400-2402.
45. - see: Hayakawa, Y.; Hirose, M.; Noyori, R. J. Org. Chem. 1993, 58, 5551-5555.
46. (a) Kodra, J. T.; Benner, S. A. Synlett 1997, 939-940.
47. (b) Jurczyk, S. C.; Horlacher, J.; Devined, K. G.; Benner, S. A.; Battersby, T. R. Helv. Chim. Acta 2000, 83, 1517-1524.
48. Gunda, P.; Russon, L. M.; Lakshman, M. K. Angew. Chem., Int. Ed. 2004, 43, 6372-6377.
49. Also see corrigendum: Gunda, P.; Russon, L. M.; Lakshman, M. K. Angew. Chem., Int. Ed. 2005, 44, 1154.
50. Lakshman, M. K.; Thomson, P. F.; Nuqui, M. A.; Hilmer, J. H.; Sevova, N.; Boggess, B. Org. Lett. 2002, 4, 1479-1482.
51. Harwood, E. A.; Hopkins, P. B.; Sigurdsson, S. T. J. Org. Chem. 2000, 65, 2959-2964.
52. Antonino, L. C.; Wu, J. C. Biochemistry 1994, 33, 1753-1759.
53. Suzuki, T.; Ide, H.; Yamada, M.; Morii, T.; Makino, K. Biorg. Med. Chem. 2001, 9, 2937-2941.
54. Bierau, J.; Leen, R.; van Gennip, A. H.; Caron, H. N.; van Kuilenburg, A. B. P. J. Chromatogr. B 2004, 805, 339-346.