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X. Guo et al.
Adenosine allyl 5’-H-phosphonate (5c). 31P NMR (122 MHz,
1
DMSO-d6, ppm): d 10.21, 9.94 (a pair of diastereomers, peak area ratio 1:1); H
3
NMR (300 MHz, DMSO-d6, ppm): d 8.31 (1H, d, H-2, JH-H = 1.38 Hz), 8.13 (1H,
3
1
d, H-8, JH-H = 4.41 Hz), 7.33–7.30 (2H, s, NH2), 6.88 (0.5H, d, P-H, JP-H = 702
1
Hz), 6.81 (0.5H, d, P-H, JP-H = 708 Hz), 5.91–5.82 (2H, m, H-1’, CH2 = CH–),
5.58 (1H, d, 3’-OH), 5.41 (1H, d, 2’-OH), 5.30–5.20 (2H, m, CH2 = CH-), 4.68–
4.60 (1H, m, H-2’), 4.48–4.46 (1H, m, H-3’), 4.25–4.15 (4H, m, H-5’,–CH2–OP),
4.08 (m, 1H, H-4’); 13C NMR (75 MHz, DMSO-d6, ppm): d 156.06 (C-6), 152.49
(C-2), 149.34 (C-4), 139.73 (C-8), 133.01 (CH2 = CH–), 118.56 (C-5), 115.20
(CH2 = CH–), 87.57 (C-1’), 82.33 (C-4’), 72.79 (C-2’), 69.91 (C-3’), 65.41
(–CH2–OP), 64.88 (C-5’); HRESI-MS: Calcd. for C13H19N5O6P [M + H]+ (m/z)
372.1073, Found 372.1081.
Uridine allyl 5’-H-phosphonate (6c). 31P NMR (122 MHz, DMSO-
d6, ppm): d 10.37, 10.02 (a pair of diastereomers, peak area ratio 1:1); 1H NMR (300
MHz, DMSO-d6, ppm): d 11.37 (1H, s, H-3), 7.63 (1H, q, H-6, 3JH-H = 7.62 Hz), 6.94
(0.5H, d, P-H, 1JP-H = 705 Hz), 6.92 (0.5H, d, P-H, 1JP-H = 708 Hz), 6.00–5.90 (1H,
m, H-1’), 5.77–5.74 (2H, m, H-5, CH2 = CH–), 5.65–5.61 (1H, d, 3’-OH), 5.51–5.48
(1H, d, 2’-OH), 5.37–5.29 (2H, m, CH2 = CH–), 4.53 (1H, m, H-2’), 4.22–4.17 (3H,
m, H-3’, –CH2–OP), 4.07 (1H, m, H-4’), 3.97 (2H, m, H-5’); 13C NMR (75 MHz,
DMSO-d6, ppm): d 163.07 (C-4), 150.71 (C-2), 140.58 (C-6), 133.08 (CH2 = CH–),
117.91 (CH2 = CH–), 102.07(C-5), 88.48 (C-1’), 81.96 (C-4’), 72.50 (C-2’), 69.48 (C-
3’), 65.58 (–CH2–OP), 64.79 (C-5’); HRESI-MS: Calcd. for C12H18N2O8P [M + H]+
(m/z) 349.0801, Found 349.0812.
Adenosine cyclohexyl 5’-H-phosphonate (5d). 31P NMR (122
MHz, DMSO-d6, ppm): d 8.77, 8.22 (a pair of diastereomers, peak area ratio 1:1);
3
1H NMR (300 MHz, DMSO-d6, ppm): d 8.30 (1H, d, H-2, JH-H = 1.71 Hz), 8.14
(1H, d, H-8, 3JH-H = 1.38 Hz), 7.29 (2H, s, NH2), 6.84 (0.5H, d, P-H, 1JP-H = 702 Hz),
6.78 (0.5H, d, P-H, 1JP-H = 699 Hz), 5.91 (1H, d, H-1’, 3JH-H = 5.16 Hz), 5.57 (1H, d,
3’-OH), 5.38 (1H, d, 2’-OH), 4.66 (1H, m, H-2’), 4.29–4.18 (3H, m, H-3’, H-5’), 4.07
(1H, m, H-4’), 3.57–3.55 (1H, m, H-5’), 1.76 (2H, br, cyclohexyl), 1.57 (2H, br,
cyclohexyl), 1.40 (3H, m, cyclohexyl), 1.17 (3H, m, cyclohexyl); 13C NMR (75
MHz, DMSO-d6, ppm): d 156.08 (C-6), 152.64 (C-2), 149.35 (C-4), 139.65 (C-8),
119.13 (C-5), 87.64 (C-1’), 82.45 (C-4’), 79.17 (C-2’), 74.85 (C-3’), 72.86 (>CH-OP),
69.85 (C-5’), 38.67 (cyclohexyl), 24.52 (cyclohexyl), 22.86 (cyclohexyl); HRESI-MS:
Calcd. for C16H27N5O6P [M + H]+ (m/z) 414.1542, Found 414.1560.
Uridine cyclohexyl 5’-H-phosphonate (6d). 31P NMR (122 MHz,
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CDCl3, ppm): d 8.46, 7.82 (a pair of diastereomers, peak area ratio 1:1); H NMR
(300 MHz, CDCl3, ppm): d 10.40 (1H, br, H-3), 7.63 (1H, q, H-6, 3JH-H = 7.92 Hz),
6.94 (0.5H, d, P-H, 1JP-H = 708 Hz), 6.93 (0.5H, d, P-H, 1JP-H = 711 Hz), 5.87 (1H, d,
H-1’), 5.76 (1H, d, H-5, 3JH-H = 6.87 Hz), 4.52–4.48 (1H, m, H-2’), 4.35–4.30 (2H, m,