TABLE 2.
Coupling constants (in Hz) for 1H NMR data of 2,3-dideoxy-2,3-difluoro sugars 9, 12 and nucleosides 20–23 with d-arabino-configurations
3J (H,H) | 3J (H,F) | ||||||||
---|---|---|---|---|---|---|---|---|---|
1,2 or 1′,2′ | 2,3 or 2′,3′ | 3,4 or 3′,4′ | 4,5a/4,5b or 4′,5′a/4′,5′b | H1,F2 or H1′,F2 | H3,F2 or H3′,F2 | H2,F3 or H2′,F3 | H4,F3 or H4′,F3 | Others | |
9 | <0.8 | 0.91 | 4.11 | n.d. | 10.03 | 19.76 | 13.44 | 22.60 | 4J 3,1 = 0.91 |
12 | <1.0 | <1.0 | 3.24 | 4.5/4.69 | 10.57 | 17.49 | 12.21 | 24.14 |
gemJ
2,F2 = 48.17 gemJ 3,F3 = 51.0 gemJ H5a,H5b = 12.71 |
20 | 3.97 | 2.17 | 3.76 | 4.27/4.85 | 17.67 | 15.29 | 12.82 | 24.80 |
5J
F2′,H8 = 2.3 4J 1′,F3′ = 1.86 gemJ 2′,F2′ = 50.52 gemJ 3′,F3′ = 51.24 J H5′a,H5′b = 12.8 |
22 | 4.76 | 3.35 | 4.73 | 4.78 | 14.54 | 16.58 | 14.77 | 22.31 |
5J
F2′,H8 = 2.27 4J 1′,F3′ = 0.9 gemJ 2′,F2′ = 50.86 gemJ 3′,F3′ = 52.16 |
21 | 2.42 | 2.74 | 3.90 | 5.04/4.98 | 15.04 | 15.90 | 14.0 | 21.16 |
gemJ
2′,F2′ = 49.70 gemJ 3′F3′ = 51.70 gemJ H5′a,H5′b = 12.8 |
23 | 3.24 | 3.37 | 4.32 | 6.30/5.26 | 15.11 | 15.39 | 17.06 | 20.44 |
gemJ
H5′a,H5′b = 2.29 gemJ 3′,F3′ = 52.35 gemJ 2′,F2′ = 50.28 |