A convenient way to N-allyloxycarbonyl protected adenosine and cytidine derivatives

Synlett

Volumn , Issue 8, 1998, Pages 853-854

  Heidenhain, Sophie B ^a   Hayakawa, Yoshihiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000584361     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1822     Document Type: Article

References (21)

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5. Hayakawa, Y.; Hirose, M.; Hayakawa, M.; Noyori, R. J. Org. Chem. 1995, 60, 925.
6. Hayakawa, Y.; Hirose, M.; Noyori, R. Nucleosides Nucleotides 1994, 13, 1337.
7. Leonard, N. J.; Neelima Nucleosides Nucleotides 1996, 15, 1369.
8. Makino, S.; Ueno, Y.; Ishikawa, M.; Hayakawa, Y.; Hata, T. Tetrahedron Lett. 1993, 34, 2775.
9. Hayakawa, Y.; Hirose, M.; Noyori, R. Tetrahedron 1995, 51, 9899.
10. Bogdan, F. M.; Chow, C. S. Tetrahedron Lett. 1998, 39, 1897.
11. Schirmeister, H.; Himmelsbach, F.; Pfleiderer, W. Helv. Chim. Acta 1993, 76, 385.
12. 6) δ 2.30-2.36 (m, 1H), 2.72-2.79 (m, 1H), 3.49-3.64 (m, 2H), 3.86-3.89 (m, 1H), 4.42-4.44 (m, 1H), 4.64-4.65 (m, 2H), 4.98-5.00 (m, 1H), 5.22-5.43 (m, 3H), 5.92-6.00 (m, 1H), 6.42-6.45 (m, 1H), 8.62 (s, 1H), 8.68 (s, 1H), 10.60 (s, 1H).
13. 6) δ 3.55-3.71 (m, 2H), 3.95-3.97 (m, 1H), 4.17 (m, 1H), 4.61-4.66 (m, 3H), 5.14-5.44 (m, 4H), 5.53 (s, 1H), 5.90-6.04 (m, 2H), 8.63 (s, 1H), 8.68 (s, 1H), 10.66 (s, 1H).
14. 6) δ 1.89-2.04 (m, 1H), 2.22-2.28 (m, 1H), 3.52-3.58 (m, 2H), 3.83-3.84 (m, 1H), 4.21 (m, 1H), 4.60-4.62 (m, 2H), 5.09-5.38 (m, 4H), 5.86-5.99 (m, 1H), 6.06-6.11 (m, 1H), 7.00-7.03 (d, 1H, J = 7.4 Hz), 8.30-8.32 (d, 1H. J = 7.4 Hz), 10.78 (s, 1H).
15. 6) δ 3.57-3.97 (m, 5H), 4.62-4.64 (m, 2H), 5.03 (d, 1H, J = 5.4 Hz), 5.15 (t, 1H, J = 4.9 Hz), 5.22-5.38 (m, 2H), 4.47 (d, 1H, J = 4.4 Hz), 5.77 (d, 1H, J = 2.4 Hz), 5.91-5.98 (m, 1H), 7.00 (d, 1H, J = 7.3 Hz), 8.40 (d, 1H, J = 7.3 Hz), 10.80 (s, 1H).
16. A similar result was reported in Watkins, B. E.; Rapoport, H. J. Org. Chem. 1982, 47, 447.
17. (a) Hakimelahi, G. H.; Proba, Z. A.; Oglivie, K. K. Can. J. Chem. 1982, 60, 1106.
18. (b) Lyttle, M. H.; Wright, P. B.; Sinha, N. D.; Bain, J. D.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4608.
19. 6) δ 3.22-3.24 (m, 2H), 3.71 (s, 6H); 4.06-4.11 (m, 1H), 4.3-4.34 (m, 1H), 4.64-4.66 (m, 2H), 4.73-4.78 (m, 1H), 5.25-5.44 (m, 3H), 5.59-5.61 (m, 1H), 5.90-6.04 (m, 2H), 6.79-6.84 and 7.18-7.36 (2 m's, 13H), 8.56 (s, 2H), 10.65 (s, 1H).
20. 6) δ 0.04 (s, 3H), 0.08 (s, 3H), 0.84 (s, 9H), 3.11-3.16 (m, 1H), 3.33-3.39 (m, 1H), 3.71 (s, 6H), 4.00-4.06 (m, 1H), 4.48-1.51 (m, 1H), 4.64-4.66 (m, 2H), 4.86-4.90 (m, 1H), 5.18-5.43 (m, 3H), 5.89-6.05 (m, 2H), 6.82-6.85 and 7.19-7.39 (2 m's, 13H), 8.54 (s, 1H), 8.57 (s, 1H), 10.67 (s, 1H).
21. 4 standard) δ 148.8, 151.0.