Table 3.
1H and 13C NMR (800/201 MHz, CDCl3) chemical shifts of triol 9.
Aa | Ba | Ca | Da | Ea | Fa | |
| ||||||
H-1 | 4.80 | 5.08 | 4.71 | 4.76 | 5.58 | 4.78 |
H-2 | 3.28 | 3.62 | 3.38 | 3.45 | 3.56 | 3.39 |
H-3 | 4.22 | 4.26 | 4.01 | 4.12 | 4.11 | 4.03 |
H-4 | 3.35 | 3.82 | 3.76 | 3.74 | 3.88 | 3.63 |
H-5 | 3.86 | 3.88 | 3.97b | 4.15b | 3.97 | 3.97b |
H-6a | 3.70 | 4.06 | 3.94c | 3.73 | 4.12c | 3.88c |
H-6b | 3.63 | 3.72 | 3.82c | 3.73 | 3.71c | 3.77c |
OH | 2.80 (bs, 1H) | – | – | 2.98 (bs, 1H) | – | – |
Bn | 5.51 (d, J = 10.8 Hz, 1H), 5.28 (d, J = 10.6 Hz, 1H), 5.17 (d, J = 10.5 Hz, 1H), 5.13 (d, J = 11.2 Hz, 1H), 4.96 (d, J = 11.0 Hz, 1H), 4.90 (2d, 2H), 4.84 (d, J = 11.5 Hz, 1H), 4.82–4.68 (m, 4H), 4.62–4.38 (m, 18H) | |||||
Ar | 7.42 (m,2H), 7.35 (m, 4H), 7.32–7.08 (m, 61H) | |||||
C-1 | 100.4 | 100.8 | 99.6 | 98.0 | 98.7 | 98.4 |
C-2 | 77.5 | 78.2 | 78.7 | 80.0 | 77.6 | 79.6 |
C-3 | 73.5 | 81.2 | 80.8 | 80.6d | 81.5d | 80.6 |
C-4 | 82.1 | 82.4 | 76.5e | 81.5e | 80.9 | 82.7 |
C-5 | 71.8 | 72.2 | 71.8f | 71.5 | 71.8f | 72.4f |
C-6 | 62.3 | 70.2 | 71.1g | 62.5 | 70.0g | 71.2g |
Bn | 76.62, 76.47, 76.03, 76.01, 74.52, 74.31, 73.48, 73.01, 72.96, 72.78, 72.62, 71.99, 69.96, 69.88, 69.82 | |||||
Ar | 139.7–137.6 (Ph ipso), 134.5–133.3 (Ar ipso), 129.9–126.6 (Ph & Ar CH) |
aThe letters A to F refers to each of the monosaccharides using normal cyclodextrin nomenclature as of Figure 1. bShifts may be interchanged. cShifts may be interchanged. dShifts may be interchanged. eShifts may be interchanged. fShifts may be interchanged. gShifts may be interchanged.