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. Author manuscript; available in PMC: 2021 Jul 2.
Published in final edited form as: J Org Chem. 2020 Jun 17;85(13):8462–8479. doi: 10.1021/acs.joc.0c00783

Table 9.

Comparison of the 13C NMR resonances of the terminal units in 10 and 15 with those of the corresponding carbons in 2/5 and 4/6a.

No 2 5 10 10vs2 10vs5 4 6 15 15vs6 15vs4
δC δC avg δC ΔδC ΔδC δC δC avg δC ΔδC ΔδC
2 84.36 83.75 85.45 1.09 1.70 81.48 80.61 82.66 2.05 1.18
3 68.10 68.29 68.51 0.41 0.22 66.97 67.05 66.92 −0.13 −0.05
4 29.04 28.90 30.17 1.13 1.27 29.90 29.55 30.55 1.00 0.65
5 156.14 156.16 156.30 0.16 0.14 156.56 156.66 156.91 0.25 0.34
6 96.20 96.22 96.56 0.36 0.34 96.12 96.14 96.54 0.40 0.42
7 152.20 152.16 152.2 0.00 0.04 152.24 152.02 152.01 −0.01 −0.23
8 106.60 106.29 106.595 0.00 0.30 107.03 106.75 106.60 −0.15 −0.43
9 151.42 150.79 151.495 0.08 0.71 152.18 151.27 152.40 1.12 0.21
10 102.89 102.58 103.41 0.52 0.83 102.21 101.66 102.19 0.53 −0.02
1’ 130.39 130.63 129.74 −0.65 −0.89 131.22 131.33 130.69 −0.64 −0.53
2’ 115.56 115.18 116.85 1.29 1.67 115.64 114.91 116.06 1.15 0.42
3’ 146.25 146.33 145.67 −0.58 −0.66 145.81 146.16 145.67 −0.49 −0.14
4’ 146.70 146.69 146.685 −0.01 0.00 146.08 146.11 146.43 0.32 0.35
5’ 116.10 116.14 117.38 1.28 1.24 115.81 115.98 116.56 0.58 0.75
6’ 120.64 120.31 120.375 −0.27 0.06 120.18 119.15 121.09 1.94 0.91
ΣΔδC 4.80 6.97 8.89 4.46
a

The 13C NMR data (100 MHz) was acquired in CD3OD with the temperature set as 255 K. With smaller ΣΔδC value.