Nucleosides and nucleotides. 138. Synthesis of 3-halo-3-deazainosines: Conformational lock with the halogen at the 3-position of the 3-deazainosine in anti-conformation

Heterocycles

Volumn 42, Issue 1, 1996, Pages 149-154

  Minakawa, Noriaki ^a   Kojinia, Naoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041679809     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-S57     Document Type: Article

References (12)

1. Part 137: S. Shuto, H. Itoh, A. Sakai, K. Nakagami, S. Imamura, and A. Matsuda, BioMed. Chem. in press (1995).
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3. b) Y. Yoshimura, B. A. Otter, T. Ueda, and A. Matsuda, Chem. Pharm. Bull., 1992, 40, 1761 and references cited therein.
4. M. Aoyagi, N. Minakawa, and A. Matsuda, Tetrahedron Lett., 1993, 34, 103.
5. N. Minakawa and A. Matsuda, Tetrahedron, 1993, 49, 557.
6. T. Umemoto, S. Fukami, G. Tomizawa, K. Harasawa, K. Kawada, and K. Tomita, J. Am. Chem. Soc., 1990, 112, 8563.
7. Y. Kobayashi, I. Kumadaki, A. Ohsawa, and S. Murakami, J. Chem. Soc., Chem. Comm., 1976, 430.
8. H. Rosemeyer, G. Toth, B. Golankiewicz, Z. Kazimierczuk, W. Bourgeois, U. Kretschmer, H.-P. Muth, and F. Seela, J. Org. Chem., 1990, 55, 5784.
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11. D. B. Davies and S. S. Danyluk, Biochemistry, 1974, 13, 4417.
12. In the crystal state, the glycosidic torsion angle of 3-methyl-3-deazainosine was -79 ° which indicated the glycosidic conformation is in the anti (χ -180 ° - -60 °), especially high anti (χ -90 ° - -60 °) region. Y. Yamagata, M. Kato, S. Fujii, M. Aoyagi, N. Minakawa, and A. Matsuda, Nucleosides Nucleotides, 1994, 13, 1327.