Molecules 2017, 22, 1710
14 of 18
6.24–6.18 (m, 1H), 5.23 (br, s, 1H), 4.91 (br, s, 1H), 4.42–4.21 (m, 4H), 4.08 (br, s, 1H), 3.82–3.75 (m, 1H),
3.64–3.41 (m, 3H), 3.11–2.98 (m, 2H), 2.69–2.59 (m, 2H), 2.19–0.98 (m, 31H), 0.98 (d, J = 6.25 Hz, 3H),
0.78 (s, 3H), 0.52 (s, 3H); 13C-NMR:
δ = 156.0 (q), 153.6 (q), 150.4 (q), 146.3 (q), 129.6 (q), 121.6 (CH),
116.8 (q), 95.1 (q), 87.6 (CH), 83.6 (CH), 71.4 (CH), 70.2 (CH), 69.9 (q), 66.0 (CH), 62.0 (CH2), 55.2 (CH),
49.8 (CH), 46.8 (CH2), 41.8 (q), 41.3 (CH), 40.3 (CH), 39.6 (CH2), 39.4 (CH), 38.9 (CH2), 36.8 (CH2), 36.0
(CH2), 35.2 (CH2), 34.6 (CH2), 32.9 (q), 32.1 (CH), 30.4 (CH2), 28.0 (CH2), 27.7 (CH2), 26.8 (CH2), 24.2
(CH2), 22.9 (CH2), 22.6 (CH3), 20.1 (CH2), 18.2 (CH2), 18.1 (CH3), 11.4 (CH3). HRMS calculated for
[C41H60N8O6 + H]+ 761.4708, found 761.4705.
dG-nor-UDC. Amorphous white solid, yield 65%; IR:
(C
C), 1687 (C=O), 1645–1523 (C=C,C=N); 1H-NMR:
5.22 (br, s, 1H), 4.89 (br, s, 1H), 4,48–4.22 (m, 4H), 3.90–3.75 (m, 3H), 3.62–3.41 (m, 2H), 3.09–2.98 (m,
1H), 2.75–2.62 (m, 2H), 2.32–0.99 (m, 33H), 0.98 (d, J = 6.25 Hz, 3H), 0.88 (s, 3H), 0.57 (s, 3H); 13C-NMR:
ν
(cm−1) 3405–3322 (O-H), 2932–2852 (C-H), 2243
= 7.87 (s, 1H), 6.48 (br, s, 2H), 6.25–6.19 (m, 1H),
≡
δ
δ
= 155.9 (q), 153.5 (q), 150.4 (q), 146.3 (q), 129.7 (q), 121.7 (CH), 116.7 (q), 95.2 (q), 87.6 (CH), 83.6 (CH),
71.0 (CH), 69.9 (q), 69.6 (CH), 69.3 (CH), 62.0 (CH2), 55.7 (CH), 54.3 (CH), 46.9 (CH2), 42.9 (q), 42.8 (CH),
42.0 (CH), 39.5 (CH2), 38.7 (CH), 37.6 (CH2), 37.1 (CH2), 36.8 (CH2), 36.1 (CH2), 34.7 (CH2), 33.6 (q),
32.8 (CH), 30.1 (CH2), 28.9 (CH2), 28.0 (CH2), 26.8 (CH2), 26.5 (CH2), 24.2 (CH2), 23.2 (CH3), 20.7 (CH2),
18.3 (CH3), 18.2 (CH2), 11.8 (CH3). HRMS calculated for [C41H60N8O6 + H]+ 761.4708, found 761.4705.
G-nor-CDC. Light yellow syrup, yield 69%; IR:
ν
(cm−1) 3409–3310 (O-H), 2926–2857 (C-H), 2243
= 10.87 (br, s, 1H), 7.89 (s, 1H), 6.52 (br, s, 2H),
(C
≡
C), 1693 (C=O), 1640–1526 (C=C,C=N); 1H-NMR:
δ
5.78 (d, J = 6.44 Hz, 1H), 5.40 (d, J = 6.25 Hz, 1H), 5,05 (br, s, 1H), 4.99–4.84 (m, 2H), 4.38–4.21 (m, 4H),
4.09 (br, s, 2H), 3.83 (br, s, 1H), 3.68–3.55 (m, 2H), 3.54–3.43 (m, 1H), 3.21–3.09 (m, 2H), 2.70–2.60 (m, 2H),
2.55–2.48 (m, 2H), 2.22–2.15 (m, 2H), 1.98–1.02 (m, 23H), 0.93 (d, J = 6.25 Hz, 3H), 0.79 (s, 3H), 0.52 (s,
3H); 13C-NMR:
δ = 156.0 (q), 153.6 (q), 150.7 (q), 146.4 (q), 130.3 (q), 121.6 (CH), 116.9 (q), 95.2 (q), 88.4
(CH), 85.5 (CH), 72.0 (CH), 70.2 (CH), 69.8 (q), 66.0 (CH), 62.1 (CH2), 55.5 (CH), 49.9 (CH), 48.2 (CH2),
41.9 (CH), 41.7 (q), 41.3 (CH), 41.0 (CH), 39.6 (CH2), 36.1 (CH), 35.2 (CH2), 34.6 (CH2), 34.1 (CH2),
33.1 (q), 32.1 (CH), 30.4 (CH2), 28.0 (CH2), 27.8 (CH2), 27.0 (CH2), 26.5 (CH2), 24.3 (CH2), 23.0 (CH2),
22.6 (CH3), 20.1 (CH2), 18.1 (CH3), 18.0 (CH2), 11.5 (CH3); HRMS calculated for [C41H60N8O7 + H]+
777.4657, found 777.4657.
G-nor-UDC. Light yellow syrup, yield 68%; IR:
ν
(cm−1) 3413–3314 (O-H), 2930–2860 (C-H), 2238
= 10.79 (br, s, 1H), 7.88 (s, 1H), 6.50 (br, s, 2H),
(C
≡
C), 1693 (C=O), 1640–1526 (C=C,C=N); 1H-NMR:
δ
5.78 (d, J = 6.44 Hz, 1H), 5.40 (d, J = 6.25 Hz, 1H), 5,05 (br, s, 1H), 4.99–4.83 (m, 2H), 4.42 (br, s, 1H),
4.39–4.18 (m, 2H), 4.04 (br, s, 1H), 3.98–3.78 (m, 2H), 3.72–3.58 (m, 1H), 3.57–3.42 (m, 1H), 2.78–2.45
(m, 4H), 1.98–0.99 (m, 30H), 0.98 (d, J = 6.25 Hz, 3H), 0.82 (s, 3H), 0.58 (s, 3H); 13C-NMR:
δ = 156.0 (q),
153.8 (q), 150.7 (q), 146.4 (q), 130.3 (q), 121.8 (CH), 116.9 (q), 95.1 (q), 88.4 (CH), 85.6 (CH), 71.0 (q), 70.7
(CH), 70.6 (CH), 69.7 (CH), 69.4 (CH), 62.1 (CH2), 55.8 (CH), 54.5 (CH), 47.0 (CH2), 43.1 (q), 43.0 (CH),
42.2 (CH), 40.0 (CH2), 38.7 (CH), 37.7 (CH2), 37.3 (CH2), 36.2 (CH2), 34.8 (CH2), 33.7 (q), 33.0 (CH), 30.2
(CH2), 28.2 (CH2), 27.0 (CH2), 26.7 (CH2), 24.4 (CH2), 23.3 (CH3), 20.8 (CH2), 18.4 (CH3), 18.3 (CH2),
11.9 (CH3); HRMS calculated for [C41H60N8O7 + H]+ 776.4658, found 776.4668.
dU-nor-CDC. Light yellow syrup, yield 71%; IR:
ν
(cm−1) 3446 (O-H), 3100–2850 (C-H), 2255 (C
≡
C),
1665 (C=O), 1634–1565 (C=C,C=N); 1H-NMR:
δ
= 8.65 (s, 1H), 7.82 (s, 1H), 6.39 (s, 1H), 6.19–6.09 (m,
1H), 5.23 (br, s, 1H), 5.10 (br, s, 1H), 4.38–4.17 (m, 3H), 4.05 (br, s, 1H), 3.86 (br, s, 1H), 3.69–3.52 (m,
3H), 3.21–3.04 (m, 1H), 2.71–2.58 (m, 3H), 2.39–2.25 (m, 1H), 2.21–2.03 (m, 1H), 2.03–0.99 (m, 30 H),
0.93 (d, J = 6.25 Hz, 3H), 0.79 (s, 3H), 0.44 (s, 3H); 13C-NMR:
δ = 158.0 (q), 153.6 (q), 146.3 (q), 136.4
(CH), 121.6 (CH), 106.2 (q), 99.7 (q), 88.0 (CH), 87.3 (CH), 70.2 (CH), 69.6 (CH), 69.5 (q), 66.0 (CH), 60.7
(CH2), 55.2 (CH), 49.9 (CH), 46.8 (CH2), 41.8 (q), 41.3 (CH), 41.1 (CH2), 40.3 (CH), 39.2 (CH2), 39.0
(CH2), 36.0 (CH2), 35.2 (CH2), 34.7 (q), 34.6 (CH2), 32.9 (CH), 32.1 (CH), 30.4 (CH2), 28.1 (CH2), 27.7
(CH2), 27.0 (CH2), 25.6 (CH2), 24.4 (CH2), 22.9 (CH2), 22.6 (CH3), 20.1 (CH2), 18.1 (CH3), 11.3 (CH3);
HRMS calculated for [C40H59N5O7 + H]+ 722.4487, found 722.4492.