Formation of 4′,5′-didehydro-5′-deoxy-3′-O-methyluridine via regioselective nucleophilic addition of methoxide anion to 2′,3′-anhydro-5′-dehydro-5′-iodouridine

Heterocycles

Volumn 67, Issue 1, 2006, Pages 399-405

  Sajiki, Hironao ^b   Takasu, Hideki ^a   Hirota, Kosaku ^b  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33747084808     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(T)14     Document Type: Article

References (46)

1. Townsend L.R. Chemistry of Nucleosides and Nucleotides (1998), Plenum, New York
2. Matsuda A. J. Synth. Org. Chem. Jpn. 48 (1990) 907
3. Perigaud C., Gosselin G., and Imbach J.-L. Nucleosides Nucleotides 11 (1992) 903
4. Maag H., Rydzewski R.M., McRoberts M.J., Crawford-Ruth D., Verheyden J.P.H., and Prisbe E.J. J. Med. Chem. 35 (1992) 1440
5. Camarasa M.-J., Perez-Perez M.-J., San-Felix A., Balzarini J., and Clercq E.D. J. Med. Chem. 35 (1992) 2721
6. Perez-Perez M.-J., San-Felix A., Balzarini J., Clercq E.D., and Camarasa M.-J. J. Med. Chem. 35 (1992) 2988
7. Clercq E.D. Med. Chem. Res. 13 (2004) 439
8. Schoeffski P. Anti-Cancer Drugs 15 (2004) 85
9. Kazimierczuk Z., Cottam H.B., Revankar G.R., and Robins R.K. J. Am. Chem. Soc. 106 (1984) 6379
10. Aoyama H. Bull. Chem. Soc. Jpn. 60 (1987) 2073
11. Okauchi T., Kubota H., and Narasaka K. Chem. Lett. (1989) 801
12. Doerr I.L., Codington J.F., and Fox J.J. J. Org. Chem. 30 (1965) 467
13. Horwitz J.P., Chua J., Rooge M.A.D., Noel M., and Klundt I.L. J. Org. Chem. 31 (1966) 205
14. Sasaki T., Minamoto K., and Hattori K. Tetrahedron 30 (1974) 2689
15. Kowollik G., and Langen P. Z. Chem. 15 (1975) 147
16. Reichman U., Hollenberg D.H., Chu C.K., Watanabe K.A., and Fox J.J. J. Org. Chem. 41 (1976) 2042
17. Hollenberg D.H., Watanabe K.A., and Fox J.J. J. Med. Chem. 20 (1977) 113
18. Hummel C.F., and Carty R.P. Nucleosides Nucleotides 2 (1983) 249
19. Misra H.K., Gati W.P., Knaus E.E., and Wiebe L.I. J. Heterocycl. Chem. 21 (1984) 773
20. Mete A., Hobbs J.B., Scopes D.I.C., and Newton R.F. Tetrahedron Lett. 26 (1985) 97
21. Ashwell M., Jones A.S., and Walker R.T. Nucleic Acids Res. 15 (1987) 2157
22. Häbich D., and Barth W. Synthesis (1988) 943
23. Wu J.-C., Pathak T., Tong W., Vial J.-M., Remaud G., and Chattopadhyaya J. Tetrahedron 44 (1988) 6705
24. Webb T.R., Mitsuya H., and Broder S. J. Med. Chem. 31 (1988) 1475
25. Matsuda A., Satoh M., Nakashima H., Yamamoto N., and Ueda T. Heterocycles 27 (1988) 2545
26. Herdewijn P., Balzarini J., Baba M., Pauwels R., Aerschot A.V., Janssen G., and Clercq E.D. J. Med. Chem. 31 (1988) 2040
27. Wu J.-C., and Chattopadhyaya J. Tetrahedron 45 (1989) 4507
28. Herdewijn P., Aerschot A.V., and Kerremans L. Nucleosides Nucleotides 8 (1989) 65
29. Perlman M.E., and Watanabe K.A. Nucleosides Nucleotides 8 (1989) 145
30. Wigerinck P., Aerschot A.V., Janssen G., Claes P., Balzarini J., Clercq E.D., and Herdewijn P. J. Med. Chem. 33 (1990) 868
31. Haraguchi K., Tanaka H., Maeda H., Itoh Y., Saito S., and Miyasaka T. J. Org. Chem. 56 (1991) 5401
32. Haung J.-T., Chen L.-C., Wang L., Kim M.-H., Warshaw J.A., Armstrong D., Zhu Q.-Y., Chou T.-C., Watanabe K.A., Matulic-Adamic J., Su T.-L., Fox J.J., Polsky B., Baron P.A., Gold J.W.M., Hardy W.D., and Zuckerman E. J. Med. Chem. 34 (1991) 1640
33. Xi Z., Agback P., Plavec J., Sandström A., and Chattopadhyaya J. Tetrahedron 48 (1992) 349
34. Minamoto K., Hamano Y., Matsuoka Y., Watanabe K., Hirota T., and Eguchi S. Nucleosides Nucleotides 11 (1992) 457
35. Ariza X., Garces J., and Vilarrasa J. Tetrahedron Lett. 33 (1992) 4069
36. Watanabe K., Yanagihara K., Minamoto K., and Iwasaki H. Nucleosides Nucleotides 12 (1993) 1061
37. Johnson R., Joshi B.V., and Reese C.B. J. Chem. Soc., Chem. Commun. (1994) 133
38. Bera S., Pathak T., and Langley G.J. Tetrahedron 51 (1995) 1459
39. Roussev C.D., Simeonov M.F., and Petkov D.D. J. Org. Chem. 62 (1997) 5238
40. Chen B.-C., Quinlan S.L., Reid J.G., and Spector R.H. Tetrahedron Lett. 39 (1998) 729
41. Liu X., and Reese C.B. J. Chem. Soc. Perkin Trans. 1 (2000) 2227
42. Haraguchi K., Itoh Y., Takeda S., Honma Y., Tanaka H., Nitanda T., Baba M., Dutschman G.E., and Cheng Y.-C. Nucleosides, Nucleotides & Nucleic Acids 23 (2004) 647
43. Codington J.F., Fecher R., and Fox J.J. J. Org. Chem. 27 (1962) 163
44. 3 as an nucleophile also provided similar 2′,5′-anhyrdo and 3′,5′-anhyrdo derivatives as a mixture. See. Hirota K., Takasu H., and Sajiki H. Heterocycles 52 (2000) 1329
45. 7
46. Hirota K., Takasu H., Tsuji Y., and Sajiki H. Chem. Commun. (1999) 1827