References
- Beaucage , S. L. and Iyer , R. P. 1993 . Tetrahedron , 49 : 1859
- Draper , D. E. and Gold , L. 1980 . Biochemistry , 19 : 1774
- Prober , J. M. , Trainor , G. L. , Dam , R. J. , Hobbs , F. W. , Robertson , C. H. , Zagursky , R. J. , Cocuzza , A. J. , Jensen , M. A. and Baumeister , K. 1987 . Science , 58 : 266
- Azhayev , A. , Guzaev , A. , Hovinen , J. , Mattinen , J. , Sillanpää , R. and Lönnberg , H. 1994 . Synthesis , 396
- Guzaev , A. , Azhayev , A. , Hovinen , J. , Azhayeva , E. and Lönnberg , H. 1994 . Bioconjugate Chem. , in the press
- Hovinen , J. , Azhayeva , E. , Azhayev , A. , Guzaev , A. and Lönnberg. , H. 1994 . J. Chem. Soc. Perkin Trans , 1 : 221
- Azhayev , A. , Guzaev , A. , Hovinen , J. , Azhayeva , E. and Lönnberg , H. 1993 . Tetrahedron Lett. , 34 : 6435
- Ono , A. , Dan , A. and Matsuda , A. 1993 . Bioconjugate Chem. , 4 : 499
- Compound 3a (45 %). 1H NMR (DMSO-d6) 11.20 (1 H, s, H3); 7.58 (1 H, s, H-6); 5.06 (1 H, d, J 3.9, exch. with D2O, 4′-OH); 4.21 (1 H, m, H-4′); 4.11 (2 H, m, H-5′ and d, H-1′ a); 3.94 (1H, dd, J6′,6 12.2, H-6′); 3.75 (1H, d, J 11.2 H-1′ b); 3.70 (1 H, dd, J5′,6 5.9, J6′,6 12.2, H-6); 3.0 - 2.8 (2H, H-3′ and H-3; overlapping with the signal of solvent); 1.77 (3H, s, 5-CH3); 1.06 (24H, 4 × i-Pr). Found: C, 53.8; H, 7.4, N, 5.3. Calcd. for C23H38N2O7Si2: C, 53.50; H, 7.50; N, 5.5 %. Compound 3b (24 %):1H NMR (DMSO-d6) 11.18 (1H, br, H-3); 7.64 (1H, s, H-6); 5.18 (1H, t, J 6.4, exch. with D2O, 1′-OH); 4.43 (1H, m, H-4′); 4.05 (1H, dd, J5′,6′3.4, J6′,6′11.7, H-6′); 3.89 (1H, dd, J5′,6′ 7.3, J6′,6′ 11.7, H-6′); 3.82 (1H, m, H-5′); 3.63 (1H, dd, JAB 11.7, J1′, OH 6.4, d upon addition of D2O, H-1′ a); 3.52 (1H, dd, J1′, OH', 6.4, d upon addition of D2O, H-1′ b); 2.65 (1H, dd, J3′,3′ 15.0, H-3′); 2.75 (1H, dd, J3′,4′ 5.8, H-3′); 1.87 (3H, s, 5-CH3); 1.02 (24H, 4 × i-Pr). Found: C, 53.7; H, 7.3, N, 5.3. Calcd. for C23H38N2O7Si2: C, 53.50; H, 7.50; N, 5.5 %.
- Compound 4b 1H NMR (DMSO-d6): 11.17 (1H, br, H-3); 8.03 (2H, 2xd, arom.); 7.71 (1H, t, arom.); 7.64 (1H, s, J > 1, H-6); 7.58 (2H, t, arom.); 5.22 (1H, d, J 3.9, exch. with D2O, 4′-OH); 4.45 (1H, dd, J5′,6′ 3.9, J6′,6′ 11.7, H-6′); 4.38 (1H, dd, J5′,6′ 4.4, J6′,6′ 11.7, H-6′); 4.24 (1H, m, H-4′); 3.75 (1H, dd, JAB 11.2, d upon addition of D2O, H-1′ a); 3.57 (1H, dd, JAB 11.2, d upon addition of D2O H-1′ b); 3.35 (1H, m, H-5′); 2.67 (1H, dd, J3′,3′ 14.1, J3′,4′ 2.9, H-3′); 2.44 (1H, dd, J3′,4′ 6.4, H-3′); 1.80 (3H, s, 5-Me). Found: C, 57.43; H, 5.47; N, 7.10. Calcd. for C18H20O7N2: C, 57.44; H, 5.36; N, 7.44. Compound 4a 1H NMR (DMSO-d6): 11.23 (1H, br, H-3); 7.88 (2H, 2xd, arom.); 7.73 (1H, d, J>1, H-6); 7.65 (1H, m, arom); 7.52 (2H, t, arom.); 5.09 (1H, d, J 3.4, exch. with D2O, 4′-OH); 4.90 (1H, t, exch. with D2O, 6′-OH); 4.90 (1H, d, J 11.2, H-1′ a); 4.47 (1H, d, J 11.2, H-1′ b); 4.19 (1H, m, H-4′); 4.02 1H, m, H-5′); 3.48 (2H, m, H-6′, H-6′); 2.77 (1H, dd, H-3′); 2.49 (1H, dd, H-3′); 1.78 (3H, s, 5-Me). Found: C, 56.91; H, 5.68; N, 7.28. Calcd. for C18H20O7N2: C, 57.44; H, 5.36; N, 7.44 %.
- Compound 7:1H NMR (D2O): 7.71 (1H, s, H-6); 4.32 (1H, m, H-4′); 4.14 (1H, m, H-5′); 3.97 (2H, m, H6′/H-6′); 3.85 (1H, d, J 12.2, H-1′ a); 3.60 (1H, d, J 12.2 H-1 'b); 2.55 (1H, dd, J3′,3′ 14.6, J3′,4′ 2.4, H-3′); 2.37 (1H, dd, J3′,4′ 6.4, H-3′); 1.72 (3H, s, 5-Me). 31P NMR (D2O): -24.32; -11.84; -8.93.
- Veeneman , G. H. , Van Der Marel , G. A. , Van Den Elst , H. and Van Boom , J. H. 1993 . Tetrahedron , 47 : 1547
- Compound 10: 1H NMR (DMSO-d6) 11.17 (1H, s, H-3), 9.40 (1H, s, CONH), 7.63 (1H, s, H-6), 5.01 (1H, d, J 3.4, exch. with D2O, 4′-OH), 4.86 (1H, t, J 5.4, exch. with D2O, 6′-OH), 4.57 (2H, AB, J 6.4 OCH2O), 4.12 (1H, m, H-4′), 4.01 (1H, d, J 10.7, H-1′ a), 3.95 (1H, m, H-5′), 3.61 (1H, d, J 10.7 H-1′ b), 3.48 (2H, t, J 5.4, OCH2), 3.38 (2H, m, H-6′ and H-6′), 3.32 (2H, m, CH2NH), 2.65 (1H, dd, J3′,3′ 14.2, J3′,4′ < 1, H-3′); 2.27 (1H, dd, J3′,4′ 6.3, H-3′); 1.80 (3H, s, 5-Me); 1.48 (2H, m, CH2); 1.25 (4H, m, 2 × CH2). Found, C, 47.0 H, 6.0. N, 8.2. Calcd. for C19H28F3N3O8: C, 47.2, H, 5.8, N, 8.7 %.