Table 2.
400 MHz 1H and 100 MHz 13C NMR data of 2 in CDCl3a.
| Position | δCb,c | δHb (J in Hz) | COSY d | NOE e | HMBC f |
|---|---|---|---|---|---|
| 1 | 38.7 t | Ha 1.07 td (12.6, 4.8) He 1.63 br d (12.6) |
He-1, H2-2 Ha-1, Ha-2 |
He-1, H-9 Ha-1, Ha-2, H3-15 |
C-3,5 |
| 2 | 19.3 t | 1.56–1.45 2H, AB type m Ha at lower field He at higher field |
H2-1, H2-3 H2-1, H2-3 |
H3-14, H3-15 Ha-1 |
C-4,10 |
| 3 | 42.0 t | Ha 1.18 td (12.4, 4.8) He 1.37 br d (12.4) |
H2-2, He-3 H2-2, Ha-3 |
He-3, H3-13 Ha-3, H3-13, H3-14 |
C-14 C-1,5,14 |
| 4 | 33.7 s | — | — | — | — |
| 5 | 55.6 d | 1.13 dd (12.8, 2.4) | H2-6 | He-6, Ha-7, H-9, H3-13 | C-6,9,10,14,15 |
| 6 | 24.6 t | Ha 1.25 qd (12.8, 3.8 )He 1.74 dm (12.8) |
H-5, He-6, H2-7 H-5, Ha-6, H2-7 |
He-6, He-7, H3-14, H3-15 H-5, Ha-6, H3-13 |
C-5,7 |
| 7 | 38.1 t | Ha 1.89 td (12.8, 5.2) He 2.28 ddd (12.8, 3.8, 2.4) |
H2-6, He-7 H2-6, Ha-7 |
H-5, He-6, He-7 Ha-6, Ha-7, Ha-12 |
C-8,12 C-5,6,8,9,12 |
| 8 | 148.9 s | — | — | — | — |
| 9 | 50.5 d | 1.77 t (4.7) | H2-11 | Ha-1, H-5 | C-8,10,6′ |
| 10 | 39.9 s | — | — | — | — |
| 11 | 34.8 t | 1.88 2H, d (4.7) | H-9 | He-1, Hb-12, H3-15 | C-8,9,10,1′,6′ |
| 12 | 107.1 t | Ha 4.75 br s Hb 4.25 br s |
Ha-7, Hb-12 Ha-12 |
He-7, Hb-12 H2-11, Ha-12, H3-15 |
C-7,9 C-7,9 |
| 13 | 33.5 q | 0.85 3H, s | H3-14 | Ha-3, H-5, He-6 | C-3,4,5,14 |
| 14 | 21.6 q | 0.75 3H, s | H3-13 | Ha-2, He-3, Ha-6, H3-15 | C-3,4,5,13 |
| 15 | 15.0 q | 0.57 3H, s | He-1, Ha-2, Ha-6, H2-11, Hb-12, H3-14 | C-1,5,9,10 | |
| 1′ | 201.2 s | — | — | — | — |
| 2′ | 134.4 d | 6.82 br s | H2-7′ | — | C-3′,4′,6′,7′ |
| 3′ | 150.9 s | — | — | — | — |
| 4′ | 196.6 s | — | — | — | — |
| 5′ | 53.1 t | Ha 3.12 d (16.0) Hb 2.97 d (16.0) |
Hb-5′ Ha-5′ |
Hb-5′, H2-11 Ha-5′ |
C-11,1′,3′,4′,6′ C-11,1′,4′,6′ |
| 6′ | 77.4 s | — | — | — | — |
| 7′ | 59.6 t | Ha 4.54 br d (17.2) Hb 4.44 br d (17.2) |
H-2′, Hb-7′ H-2′, Ha-7′ |
Hb-7′ Ha-7′ |
C-2′,3′ C-2′,3′ |
| 6′-OH | — | 3.87 br s | — | C-1′,5′,6′ | |
| 7′-OH | — | 3.48 br s | — |
a The 1H and 13C NMR signals were assigned on the basis of DEPT, 1H–1H COSY, HMQC, HMBC, NOESY, and 1D difference NOE experiments; b Chemical shift values (δH and δC) were recorded using the solvent signals (CDCl3: δH7.26/δC77.1) as references, respectively; Ha: axial proton; He: equatorial proton; c Multiplicities of the carbon signals were determined by DEPT experiments and are shown as s (singlet), d (doublet), t (triplet) and q (quartet), respectively; d The numbers in each line of this column indicate the protons that correlated with the proton in the corresponding line in 1H–1H COSY; e The numbers in each line of this column indicate the protons that showed NOE correlations with the proton in the corresponding line in NOESY or 1D difference NOE experiments. The NOEs between two protons in a spin coupling relationship were detected by the 1D difference NOE experiments; f The numbers in each line of this column indicate the carbons that showed HMBC correlations with the proton in the corresponding line in the HMBC experiments optimized for the 8.3 Hz of long-range JCH value.