Table 3.
1H NMR Data (chemical shifts in ppm) for HMVK adducts with NAL
| HMVK-NAL Adduct 1 | HMVK-NAL Adduct 2 | HMVK-NAL Adduct 3 | |
|---|---|---|---|
| C-1a | 2.00 (s, 3H)b | 2.00 (s, 3H) | 1.92 (s, 3H), (22c) |
| C-3 | 4.28 (m, 1H) | 4.26 (s, br, 1H) | 4.05 (m, 1H), (55) |
| C-5−7 | 1.44, 1.69 (m, 6H) | 1.40, 1.72, 1.85 (m, 6H) | 1.30, 1.65 (m, 6H), (22, 24, 31) |
| C-8 | 2.93 (t, 2H) | 2.45 (t, 2H) | 2.53 (s, br, 2H), (23) |
| C-9 | 3.04 (t, 2H) | 3.57 (s, 2H) | 3.65 (m, 2H), (47) |
| C-10 | 3.29 (t, 2H) | 3.15 (m, 4H)d | 2.96 (m, 2H), (57) |
| C-12 | 4.35 (s, 2H) | 2.60 (s, 1H) | - |
| C-14 | - | 3.40 (d, 1H), 3.61 (d, 1H) | 5.17 (s, 1H), (91) |
| C-15 | - | 3.15 (m, 4 H) | 3.15 (m, 2H), (48) |
| C-16 | - | 3.70 (d, 1H), 3.91 (d, 1H) | 4.37 (d, 1H), 4.55 (d, 1H), (62) |
a
For structural assignments, see the scheme shown in Figure 7
b
Multiplicities and integration, respectively, are listed in parenthesis
c
Chemical shift of C based on HSQC NMR for HMVK-NAL Adduct 3
d
Protons of C-10 and C-15 are part of the same multiplet for adduct 2