8 of 11
TACHALLAIT ET AL.
|
(3R,4R)-2-(Acetoxymethyl)-5-(3-((1-((2R,3S,4S,5S)-3,4-
3H), 2.04 (s, 6H), 1.98 (s, 3H); 13C NMR (101 MHz, CDCl3, δ, ppm):
170.11, 169.57, 169.54, 161.78, 159.84, 150.51, 143.08, 137.50,
129.72, 126.58, 123.04, 114.41, 102.71, 88.65, 79.72, 72.94, 69.93,
62.90, 55.31, 53.63, 36.17, 20.76, 20.47, 20.40; MS (ESI+): m/z = 572.3
[M+H]+, 1143 [2M+H]+.
diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)-1H-1,2,3-
triazol-4-yl)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-
tetrahydrofuran-3,4-diyl diacetate (6c)
Yield 95%. Colorless oil; Rf = 0.35 (cyclohexane/AcOEt 1:4); 1H NMR
(400 MHz, CDCl3, δ, ppm): 7.74 (s, 1H), 7.32 (d, J = 8.2 Hz, 1H), 6.06 (d,
J = 4.0 Hz, 1H), 5.96 (d, J = 4.8 Hz, 1H), 5.76 (d, J = 8.1 Hz, 1H), 5.71 (dd,
J = 5.2, 4.0 Hz, 1H), 5.53 (t, J = 5.2 Hz, 1H), 5.30–5.23 (m, 2H), 5.19 (q,
2H), 4.38 (dd, J = 8.2, 4.2 Hz, 1H), 4.32 (dd, J = 12.3, 3.2 Hz, 1H), 4.28
(q, J = 1.6 Hz, 3H), 4.15 (dd, J = 12.3, 4.2 Hz, 1H), 2.06 (s, 3H), 2.04 (d,
J = 1.1 Hz, 6H), 2.03 (s, 6H), 2.02 (s, 3H); 13C NMR (101 MHz, CDCl3, δ,
ppm): 170.48, 170.11, 169.62, 169.55, 169.40, 169.20, 161.72,
150.54, 143.30, 137.46, 122.79, 102.72, 89.97, 88.49, 80.98, 79.78,
74.40, 72.92, 70.83, 69.96, 62.93, 62.90, 35.99, 20.78, 20.70, 20.49,
20.44, 20.42; MS (ESI+): m/z = 710.1 [M+H]+.
2-(Acetoxymethyl)-5-(3-((1-((4R,6S)-6-(hydroxymethyl)-2,2-
dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1H-1,2,3-triazol-
4-yl)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-
tetrahydrofuran-3,4-diyl diacetate (6g)
Yield 73%. Orange oil; Rf = 0.32 (cyclohexane/AcOEt 1:4); 1H NMR
(400 MHz, CDCl3, δ, ppm): 7.78 (s, 1H), 7.33 (d, J = 8.1 Hz, 1H), 6.00 (s,
1H), 5.91 (d, J = 4.6 Hz, 1H), 5.76 (d, J = 8.1 Hz, 1H), 5.31 (t, J = 5.3 Hz,
1H), 5.27–5.24 (m, 1H), 5.15 (s, 3H), 4.94 (d, J = 5.8 Hz, 1H), 4.44 (s,
1H), 4.28 (d, J = 1.7 Hz, 3H), 3.71 (d, J = 12.5 Hz, 1H), 3.56 (d,
J = 12.4 Hz, 1H), 2.05 (s, 3H), 2.04 (s, 3H), 2.02 (s, 3H), 1.51 (s, 3H),
1.29 (s, 3H); 13C NMR (101 MHz, CDCl3, δ, ppm): 170.16, 169.78,
169.62, 161.74, 150.51, 137.79, 123.70, 113.57, 102.65, 95.23,
89.02, 88.94, 85.64, 81.85, 79.72, 73.03, 69.94, 63.23, 62.87, 60.37,
35.93, 27.01, 25.09, 20.76, 20.47, 20.44; MS (ESI+): m/z = 624.1
[M+H]+, 1247.1 [2M+H]+.
(2R,3R,4S,5R)-2-(Acetoxymethyl)-6-(4-((3-((3R,4R)-3,4-
diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)-2,6-dioxo-
3,6-dihydropyrimidin-1(2H)-yl)methyl)-1H-1,2,3-triazol-1-yl)-
tetrahydro-2H-pyran-3,4,5-triyl triacetate (6d)
Yield 94%. Colorless oil; Rf = 0.41 (cyclohexane/AcOEt 1:4); 1H NMR
(400 MHz, CDCl3, δ, ppm): 7.79 (s, 1H), 7.34 (dd, J = 14.2, 8.2 Hz, 1H),
5.98 (dd, J = 14.3, 4.9 Hz, 1H), 5.82–5.73 (m, 1H), 5.67 (d, J = 9.4 Hz,
1H), 5.38–5.29 (m, 1H), 5.30 (d, J = 5.4 Hz, 1H), 5.29–5.20 (m, 1H),
5.22–5.12 (m, 2H), 5.08 (dd, J = 18.2, 14.7 Hz, 1H), 4.28 (d, J = 2.3 Hz,
3H), 4.20 (td, J = 13.1, 5.1 Hz, 1H), 4.15–4.02 (m, 1H), 3.96–3.87 (m,
1H), 2.07 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 1.95
(s, 3H), 1.77 (s, 3H); 13C NMR (101 MHz, CDCl3, δ, ppm): 170.54,
170.12, 169.92, 169.59, 169.32, 168.82, 168.43, 161.64, 150.57,
143.60, 137.44, 122.13, 102.73, 88.67, 85.66, 79.78, 75.13, 73.02,
72.67, 70.25, 69.92, 67.70, 62.89, 61.60, 35.96, 20.77, 20.72, 20.55,
20.51, 20.45, 20.34, 20.13; MS (ESI+): m/z = 782.1 [M+H]+.
2-(Acetoxymethyl)-5-(2,4-dioxo-3-((1-((2R,4R,5S)-5-(2-oxo-2-
(p-tolyloxy)ethyl)-4-((p-tolyloxy)carbonyl)tetrahydrofuran-2-yl)-
1H-1,2,3-triazol-4-yl)methyl)-3,4-dihydropyrimidin-1(2H)-yl)-
tetrahydrofuran-3,4-diyl diacetate (6h)
Yield 77%. Colorless oil; Rf = 0.60 (cyclohexane/AcOEt 1:4); 1H NMR
(400 MHz, CDCl3, δ, ppm): 7.86 (d, J = 7.0 Hz, 3H), 7.65 (d, J = 8.8 Hz,
2H), 7.29 (d, J = 8.2 Hz, 1H), 7.18 (t, J = 8.4 Hz, 4H), 6.38 (d, J = 6.7 Hz,
1H), 5.92 (d, J = 4.7 Hz, 1H), 5.74 (d, J = 8.1 Hz, 1H), 5.56 (d, J = 6.9 Hz,
1H), 5.28 (t, J = 5.4 Hz, 1H), 5.21 (d, J = 13.3 Hz, 2H), 5.09 (d,
J = 14.4 Hz, 1H), 4.71 (s, 1H), 4.52 (qd, J = 12.2, 3.8 Hz, 2H), 4.26 (s,
3H), 3.05 (d, J = 15.0 Hz, 1H), 3.01–2.88 (m, 1H), 2.35 (s, 3H), 2.33 (s,
3H), 2.05 (s, 3H), 2.03 (s, 3H), 1.99 (s, 3H); 13C NMR (101 MHz, CDCl3,
δ, ppm): 170.08, 169.54, 169.53, 166.12, 166.01, 161.70, 150.54,
144.35, 144.18, 142.95, 137.35, 129.78, 129.69, 129.30, 126.73,
126.20, 121.86, 102.71, 89.78, 88.66, 84.48, 79.70, 74.40, 72.99,
69.90, 63.93, 62.87, 38.63, 36.11, 21.74, 21.72, 20.77, 20.47, 20.42;
MS (ESI+): m/z = 804.2 [M+H]+.
2-(Acetoxymethyl)-5-(3-((1-(naphthalen-2-ylmethyl)-1H-1,2,3-
triazol-4-yl)methyl)-2,4-dioxo-3,4 dihydropyrimidin-1(2H)-yl)-
tetrahydrofuran-3,4-diyl diacetate (6e)
Yield 78%. Yellow oil; Rf = 0.28 (cyclohexane/AcOEt 1:4); 1H NMR
(400 MHz, CDCl3, δ, ppm): 7.76–7.73 (m, 3H), 7.66 (s, 1H), 7.47 (s, 1H),
7.45–7.39 (m, 2H), 7.28 (t, J = 8.2 Hz, 2H), 5.93 (d, J = 4.6 Hz, 1H), 5.71
(d, J = 8.3 Hz, 1H), 5.55 (s, 2H), 5.29–5.18 (m, 3H), 5.11 (s, 2H), 4.25 (s,
3H), 2.02 (s, 7H), 1.93 (s, 3H); 13C NMR (101 MHz, CDCl3, δ, ppm):
170.10, 169.57, 169.54, 161.76, 150.54, 143.29, 137.49, 133.19,
133.15, 131.98, 129.08, 127.97, 127.75, 127.45, 126.63, 125.46,
123.38, 102.71, 88.59, 79.73, 72.93, 69.95, 62.91, 54.29, 53.50,
36.19, 20.76, 20.48, 20.36; MS (ESI+): m/z = 592.3 [M+H]+.
2-(Acetoxymethyl)-5-(3-((1-(4-nitrophenethyl)-1H-1,2,3-triazol-
4-yl)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-
tetrahydrofuran-3,4-diyl diacetate (6i)
Yield 82%. White oil; Rf = 0.30 (cyclohexane/AcOEt 1:4); 1H NMR
(400 MHz, CDCl3, δ, ppm): 8.03 (d, J = 8.6 Hz, 2H), 7.30 (d, J = 8.2 Hz,
1H), 7.24 (s, 1H), 7.12 (d, J = 6.6 Hz, 2H), 5.90 (d, J = 4.5 Hz, 1H), 5.72 (d,
J = 8.2 Hz, 1H), 5.38–5.23 (m, 2H), 5.11 (q, 2H), 4.52 (t, J = 6.9 Hz, 2H),
4.29 (s, 3H), 3.24 (t, J = 7.2 Hz, 2H), 2.07 (s, 3H), 2.05 (s, 3H), 2.02 (s,
3H); 13C NMR (101 MHz, CDCl3, δ, ppm): 170.18, 169.63, 169.60,
161.66, 150.42, 147.13, 144.58, 142.85, 137.82, 129.68, 123.97,
123.96, 102.53, 89.10, 79.78, 76.74, 72.96, 69.97, 62.89, 50.75,
36.43, 36.01, 20.79, 20.47, 20.47; MS (ESI+): m/z = 601.3 [M+H]+,
1201.1 [2M+H]+.
2-(Acetoxymethyl)-5-(3-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-
4-yl)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-
tetrahydrofuran-3,4-diyl diacetate (6f)
Yield 91%. Colorless oil; Rf = 0.24 (cyclohexane/AcOEt 1:4); 1H NMR
(400 MHz, CDCl3, δ, ppm): 7.41 (s, 1H), 7.30 (d, J = 8.3 Hz, 1H), 7.14 (d,
J = 8.8 Hz, 2H), 6.80 (d, J = 8.7 Hz, 2H), 5.94 (s, 1H), 5.73 (d, J = 8.2 Hz,
1H), 5.33 (s, 2H), 5.26 (s, 2H), 5.14–5.08 (m, 2H), 4.27 (s, 3H), 3.72 (s,