Vol. 27, No. 1 (2015)
Synthesis of Novel Glycosyl Imidazolidine-2,4,5-Trione Derivatives 163
1406, 1217, 1038; 1H NMR (DMSO-d6, 300 MHz) δ: 7.35 (d,
J = 8.3 Hz, 2H, ArH), 7.24 (d, J = 8.3 Hz, 2H, ArH), 6.14 d, J
= 8.9 Hz, 1H, H1), 5.89-5.50 (m, 1H, H3), 5.01 (m, 1H, H4),
4.25 (m, 3H, H5, H6, H6'), 4.11-3.94 (m, 1H, H2), 2.36 (s,
3H, CH3), 1.99 (4s, 12H, Ac); 13C NMR (CDCl3-d6, 75 MHz)
δ: 171.19, 170.93, 169.67, 169.22, 156.39, 154.92, 152.47,
139.95, 130.36, 127.20, 126.13, 89.78, 72.63, 70.98, 67.75,
61.43, 55.31, 21.53, 21.21, 21.02, 20.88, 20.82; ESI-MS (m/z):
calcd for [M + Na]+ C24H26N2O12Na: 557.1378, found
557.1382.
130.63, 118.38, 115.30, 112.25, 89.77, 72.68, 71.03, 67.74,
61.47, 55.83, 55.37, 21.23, 21.04, 20.90, 20.84; ESI-MS (m/z):
Calcd. for [M + Na]+ C24H26N2O13Na: 573.1327, found
573.1332.
1-(2-Methoxyphenyl)-3-(1,3,4,6-tetra-O-acetyl-2-deoxy-
β-D-glucopyranos-2-yl)imidazolidine-2,4,5-trione (3n).
White solid, m.p. 90-93 °C; IR (KBr, νmax, cm-1): 2946, 1745,
1
1600, 1508, 1465, 1404, 1221, 1039; H NMR (DMSO-d6,
300 MHz) δ: 7.52 (dd, J = 10.9, 4.9 Hz, 1H, ArH), 7.27 (m,
2H, ArH), 7.14-7.02 (m, 1H, ArH), 6.27 (d, J = 8.9 Hz, 0.58H,
H1), 6.20 (d, J = 8.9 Hz, 0.40 H, H1), 5.80-5.62 (m, 1H, H3),
5.13-4.97 (m, 1H, H4), 4.38-4.12 (m, 3H, H5, H6, H6'), 4.04
(m, 1H, H2), 3.77 (s, 3H, CH3O), 2.13-1.90 (m, 12H, Ac); 13C
NMR (CDCl3-d6, 75 MHz) δ: 170.98, 169.72, 168.81, 156.39,
155.06, 151.96, 132.19, 129.69, 129.53, 121.39, 118.01,
112.65, 89.62, 72.97, 70.53, 68.24, 67.88, 61.58, 56.31, 55.15,
21.15, 21.08, 20.94, 20.85, 20.79; ESI-MS (m/z): Calcd. for
[M + Na]+ C24H26N2O13Na: 573.1327, found 573.1331.
1-(3,4,5-Trimethoxyphenyl)-3-(1,3,4,6-tetra-O-acetyl-
2-deoxy-β-D-glucopyranos-2-yl)imidazolidine-2,4,5-trione
(3o): White solid, m.p. 99-101 °C; IR (KBr, νmax, cm-1): 2946,
1-(m-Tolyl)-3-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-
glucopyranos-2-yl)imidazolidine-2,4,5-trione (3j): White
solid, m.p. 90-91 °C; IR (KBr, νmax, cm-1): 2960, 1738, 1610,
1
1494, 1403, 1218, 1038; H NMR (DMSO-d6, 300 MHz) δ:
7.43 (m, 1H, ArH), 7.30 (d, J = 7.4 Hz, 1H, ArH), 7.16 (d, J =
8 Hz, 2H, ArH), 6.14 (d, J = 8.8 Hz, 1H, H1), 5.74 (mz, 1H,
H3), 5.01 (m, 1H, H4), 4.37-4.12 (m, 3H, H5, H6, H6'), 4.09-
3.92 (m, 1H, H2), 2.37 (s, 3H, CH3), 2 (4s, 12H, Ac). 13C
NMR (CDCl3-d6, 75 MHz) δ: 171.24, 170.94, 169.65, 169.17,
156.33, 154.83, 152.37, 139.98, 130.57, 129.58, 126.80,
123.37, 89.82, 72.71, 71.06, 67.75, 61.48, 55.38, 21.64, 21.22,
21.03, 20.89, 20.83; ESI-MS (m/z): Calcd. for [M + Na]+
C24H26N2O12Na: 557.1378, found 557.1381.
1
2837, 1742, 1600, 1508, 1465, 1406, 1232, 1038; H NMR
(CDCl3-d6, 300 MHz) δ: 6.63 (s, 2H, ArH), 6.44 (d, J = 8.7
Hz, 1H, H1), 5.70 (t, 1H, H3), 5.26 (dd, J = 16.3, 6.5 Hz, 1H,
H4), 4.48-4.27 (m, 2H, H5, H6), 4.13 (d, J = 12.6 Hz, 1H,
H6'), 4.02-3.76 (m, 10 H, H2, 3CH3O), 2.08 (4s, 12 H, Ac);
13C NMR (CDCl3-d6, 75 MHz) δ: 171.39, 170.95, 169.60,
169.11, 156.14, 154.81, 153.94, 152.31, 139.02, 125.12, 104),
89.85, 72.87, 71.26, 67.69, 61.53, 61.24, 56.63, 55.54, 21.24,
21.05, 20.91; ESI-MS (m/z): Calcd. for [M + Na]+
C26H30N2O15Na: 633.1538, found 633.1537.
1-(o-Tolyl)-3-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-
glucopyranos-2-yl)imidazolidine-2,4,5-trione (3k): White
solid, m.p. 90-92 °C; IR (KBr, νmax, cm-1): 2961, 1744, 1498,
1
1403, 1218, 1038; H NMR (DMSO-d6, 300 MHz) δ: 7.34
(m, 4H, ArH), 6.23 (d, J = 9 Hz, 1H, H1), 6.06 (d, J = 8.1 Hz,
1H, H1), 5.88-5.73 (m, 1H, H3), 5.72-5.56 (m, 1H, H3), 5.02
(m, 1H, H4), 4.27 (m, 3H, H5, H6, H6'), 4.11-3.96 (m, 1H,
H2), 2.16 (d, J = 13.4 Hz, 3H, CH3), 2.09-1.87 (m, 12H, Ac);
13C NMR (CDCl3-d6, 75 MHz) δ: 170.99, 169.65, 169.22,
169.09, 156.48, 154.87, 152.23, 136.32, 131.81, 130.81,
128.38, 127.51, 89.79, 72.80, 70.99, 67.83, 67.65, 61.51,
55.55, 21.18, 21.06, 20.92, 20.85, 17.86; ESI-MS (m/z): Calcd.
for [M + Na]+ C24H26N2O12Na: 557.1378, found 557.1382.
1-(4-Methoxyphenyl)-3-(1,3,4,6-tetra-O-acetyl-2-
deoxy-β-D-glucopyranos-2-yl)imidazolidine-2,4,5-trione
(3l). White solid, m.p. 89-91 °C; IR (KBr, νmax, cm-1): 2961,
1-(2,5-Dimethoxyphenyl)-3-(1,3,4,6-tetra-O-acetyl-2-
deoxy-β-D-glucopyranos-2-yl)imidazolidine-2,4,5-trione
(3p): White solid, m.p. 97-99 °C; IR (KBr, νmax, cm-1): 2961,
1
2842, 1747, 1593, 1513, 1465, 1400, 1228, 1038; H NMR
(CDCl3-d6, 300 MHz) δ: 7.06-6.89 (m, 2H, ArH), 6.80 (m,
1H, ArH), 6.41 (d, J = 8.8 Hz, 1H, H1), 5.88-5.61 (m, 1H,
H3), 5.21 (m, 1H, H4), 4.51-4.25 (m, 2H, H5, H6), 4.11 (m,
1H, H6'), 4.03-3.88 (m, 1H, H2), 3.83-3.70 (m, 6H, 2CH3O),
1
13
1731, 1608, 1497, 1397, 1212, 1036; H NMR (DMSO-d6,
2.19-1.91 (m, 12 H, Ac); C NMR (CDCl3-d6, 75 MHz) δ:
300 MHz) δ: 7.27 (d, J = 8.8 Hz, 2H, ArH), 7.09 (d, J = 8.9
Hz, 2H, ArH), 6.14 (d, J = 8.8 Hz, 1H, H1), 5.84-5.52 (m, 1H,
H3), 5.01 (m, 1H, H4), 4.38-4.11 (m, 3H, H5, H6, H6'), 4.03
(d, J = 11.2 Hz, 1H, H2), 3.80 (s, 3H, CH3O), 2 (4s, 12H, Ac);
13C NMR (CDCl3-d6, 75 MHz) δ: 171.29, 170.98, 169.65,
169.15, 160.43, 156.38, 155.02, 127.73, 122.22, 115.03, 89.84,
72.79, 71.15, 67.72, 61.50, 55.91, 55.40, 21.26, 21.07, 20.93,
20.87; ESI-MS (m/z): Calcd. for [M + Na]+ C24H26N2O13Na:
573.1327, found 573.1332.
1-(3-Methoxyphenyl)-3-(1,3,4,6-tetra-O-acetyl-2-
deoxy-β-D-glucopyranos-2-yl)imidazolidine-2,4,5-trione
(3m). White solid, m.p. 91-93 °C; IR (KBr, νmax, cm-1): 2958,
1746, 1603, 1508, 1467, 1405, 1216, 1040; 1H NMR (CDCl3-
d6, 300 MHz) δ: 7.41 (t, 1H, ArH), 7.05-6.84 (m, 3H, ArH),
6.44 (d, J = 8.8 Hz, 1H, H1), 5.70 (t, 1H, H3), 5.25 (t, 1H,
H4), 4.50-4.26 (m, 2H, H6, 5), 4.13 (d, J = 12.2 Hz, 1H, H6'),
3.97 (d, J = 8.1 Hz, 1H, H2), 3.84 (s, 3H, CH3O), 2.21-1.89
(4s, 12 H, Ac); 13C NMR (CDCl3-d6, 75 MHz) δ: 171.24,
170.96, 169.67, 169.21, 160.48, 156.24, 154.71, 152.23,
170.94, 169.74, 168.86, 156.36, 154.98, 153.89, 151.86
(s, 1H), 149.19, 118.33, 117.19, 115.19, 113.60, 89.56, 72.85,
70.46, 68.26, 67.89, 61.54, 56.78, 56.20, 55.12 (s, 2H), 21.12,
21.04, 20.90, 20.82, 20.75; ESI-MS (m/z): Calcd. for [M +
Na]+ C25H28N2O14Na: 603.1433, found 603.1437.
1-(Naphthalen-1-yl)-3-(1,3,4,6-tetra-O-acetyl-2-deoxy-
β-D-glucopyranos-2-yl)imidazolidine-2,4,5-trione (3q):
Yellow solid, m.p. 114-116 °C; IR (KBr, νmax, cm-1): 2961,
1748, 1600, 1512, 1470, 1406, 1223, 1037; 1H NMR (DMSO-
d6, 300 MHz) δ: 8.23-7.89 (m, 3H, ArH), 7.72-7.49 (m, 4H,
ArH), 6.24 (d, J = 8.8 Hz, 1H, H1), 5.93-5.82 (m, 1H, H3), 5.72
(m, 1H, H3), 5.01 (m, 1H, H4), 4.43-4.11 (m, 3H, H5, H6, H6'),
4.03 (d, J = 11.8 Hz, 1H, H2), 2.12-1.91 (m, 12H,Ac); 13C NMR
(CDCl3-d6, 75 MHz) δ: 171.69, 171.36, 170.98, 169.65, 169.41),
169.19, 156.59, 156.53, 155.56, 155.38, 134.73, 131.42, 129.79,
129.07, 128.15, 127.33, 127.07, 126.93, 126.03, 125.66, 121.84,
90.08, 72.79, 71.41, 67.76, 67.59, 61.51, 55.78, 21.30, 21.08,
21.01, 20.94; ESI-MS (m/z): Calcd. for [M + Na]+
C27H26N2O12Na: 593.1378, found 593.1383.