Table 2. 13C NMR chemical shifts (p.p.m.) of 2, 4, 6a and 6b in CDCl3 at 27°C.
Chemical shifta | Compound | |||
---|---|---|---|---|
2 | 4 | 6a | 6b | |
C-1′ | 88.68 | 90.73 | 89.41 | 89.63 |
C-2′ | 74.61 | 75.97 | 76.05 | 75.86 |
C-3′ | 71.56 | 72.33 | 72.71 | 72.60 |
C-4′ | 84.86 | 85.95 | 85.52 | 85.53 |
C-5′ | 63.87 | 63.58 | 6 3.78 | 63.75 |
C-6 | 153.06 | 155.27 | 147.30 | 145.91 |
C-4 | 144.00 | 147.42 | 143.26 | 143.15 |
C-5 | 121.37 | 119.97 | 123.06 | 122.71 |
C-2 | 147.24 | 152.59 | 147.85 | 147.99 |
C-8 | 139.93 | 137.72 | 135.06 | 135.09 |
1-Me | 37.67 | 36.84 | 36.90 | |
6-R | 27.31 | 37.20 | 43.59 | |
16.95 | ||||
NOEDIF | ↓1-Me→ | ↓6-Me→ | ↓H-2→ | ↓1-Me→ |
H-2↑(2%) | H-2(no NOE) | 1-Me↑(2%) | H-2↑(2%) | |
GHMBC | 1-Me→H-2 | C-5→H-8 | 1-Me→H-2 | 1-Me→H-2 |
C-5→H-8 | C-8→H-1′ | C-5→H-8 | C-5→H-8 | |
C-8→H-1′ | C-8→H-1′ | C-8→H-1′ | ||
C-6→1-Me C-2→1-Me | C-6→6-Me + 1-Me | C-6→6-CH2 + 1-Me | ||
C-2→1-Me | C-2→1-Me |
aTypical shifts of the monomethoxytrityl group: 158.70, 144.08, 135.18, 130.42, 128.38, 127.90, 127.05, 113.23, 86.83 and 55.24.