Table 1.
1H [600 MHz, δ in ppm, Mult. (J in Hz)] and 13C NMR (150 MHz, δ in ppm) data of 1–3 in CDCl3. −aNo signal observed in 1H NMR and 13C NMR spectra.
| No. | 1 | 2 | 3 | |||
|---|---|---|---|---|---|---|
| δ H (mult., J, in Hz) | δ C | δ H (mult., J, in Hz) | δ C | δ H (multi, J, in Hz) | δ C | |
| 1 | 7.05 (s) | 104.2 | 7.03 (s) | 104.1 | 7.01 (s) | 104.0 |
| 2 | 147.5 | 147.4 | 147.2 | |||
| 3 | 147.9 | 148.0 | 147.4 | |||
| 4 | 6.85 (s) | 100.8 | 6.77 (s) | 100.8 | 5.29 (br s) | 100.5 |
| 4a | 127.6 | 127.8 | 127.1 | |||
| 4b | 139.4 | 139.4 | 139.5 | |||
| 6 | 5.13 (d, 9.0) | 58.0 | 5.14 (d, 10.3) | 57.8 | −a | 63.8 |
| 6a | 126.7 | 127.0 | 125.6 | |||
| 7 | 146.3 | 146.3 | 146.8 | |||
| 8 | 152.1 | 152.0 | 152.1 | |||
| 9 | 6.68 (br d, 7.3) | 111.7 | 6.66 (br s) | 111.5 | 6.84 (d, 8.4) | 112.6 |
| 10 | 7.23 (br d, 7.3) | 116.6 | 7.23 (br s) | 118.5 | 7.39 (d, 8.4) | 118.9 |
| 10a | 125.0 | 125.0 | 125.4 | |||
| 10b | 124.3 | 124.5 | 124.0 | |||
| 11 | 7.61 (d, 8.5) | 119.8 | 7.63 (d, 8.5) | 119.9 | 7.78 (d, 8.4) | 119.8 |
| 12 | 7.46 (d, 8.5) | 123.8 | 7.45 (d, 8.5) | 123.7 | 7.48 (d, 8.4) | 124.2 |
| 12a | 131.0 | 130.8 | 130.9 | |||
| 1′ | 6.83 (s) | 111.7 | 6.92 (s) | 112.1 | −a | −a |
| 2′ | 145.6 | 145.4 | −a | |||
| 3′ | 148.3 | 147.8 | −a | |||
| 4′ | 6.21 (s) | 109.8 | 6.19 (s) | 109.7 | 5.89 (s) | 110.8 |
| 4′a | 133.7 | 134.1 | −a | |||
| 5′ | 2.37–2.31 (m) 1.93 (br s) | 33.4 | 2.50–2.33 (m) 1.86–1.65 (m) | 33.7 | 2.23–1.59 (m) | −a |
| 6′ | 2.37–2.31 (m) 1.85 (br s) | 56.9 | 2.50–2.33 (m) 1.86–1.65 (m) | 57.2 | 2.23–1.59 (m) | −a |
| 8′ | 3.07 (d, 13.2) 2.32 (br s) | 48.5 | 3.09 (d, 13.3) 2.50–2.33 (m) | 48.3 | 3.21 (br s) 3.02 (br s) | −a |
| 8′a | 118.5 | 130.6 | −a | |||
| 9′ | 145.0 | 147.0 | −a | |||
| 10′ | 146.0 | 150.5 | 150.1 | |||
| 11′ | 6.97 (br d, 8.0) | 107.1 | 7.07 (d, 8.3) | 110.8 | 6.81 (d, 6.6) | 107.7 |
| 12′ | 7.50 (br s) | 122.5 | 7.61 (d, 8.3) | 125.2 | 7.83 (br s) | −a |
| 12′a | 132.9 | 132.1 | −a | |||
| 13′ | 4.59 (d, 9.0) | 52.8 | 4.47(d, 10.3) | 52.9 | 5.01 (br s) | −a |
| 14′ | −a | −a | −a | |||
| 14′a | 135.5 | 135.6 | −a | |||
| 5-N-CH3 | 2.51 (s) | 41.1 | 2.50 (s) | 40.8 | 2.56 (s) | 43.1 |
| 7′-N-CH3 | 1.63 (s) | 41.7 | 1.49 (s) | 41.5 | 1.89 (s) | 41.4 |
| 2,3-OCH2O- | 5.99 (d, 1.1) 5.96 (d, 1.1) | 101.1 | 5.93–5.81 (m) | 101.0 | 5.99–5.76 (m) | 101.1 |
| 7-OCH3 | 3.94 (s) | 61.0 | 3.93 (s) | 61.8 | 3.77 (s) | 61.1 |
| 8-OCH3 | 3.83 (s) | 55.9 | 3.81 (s) | 55.7 | 3.65 (s) | 56.1 |
| 2′,3′-OCH2O- | 5.91 (d, 1.1) 5.83 (d, 1.1) | 101.1 | 5.93–5.81 (m) | 100.9 | 5.99–5.76 (m) | 101.6 |
| 9′,10′-OCH2O- or –OCH3 | 5.87 (d, 1.4) 5.82 (d, 1.4) | 100.6 | 3.50 (s) 3.95 (s) | 60.9 56.0 | 5.99–5.76 (m) | 100.9 |