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T. G. Barros et al.
PAPER
1,4:3,6-Dianhydro-2-{[(Z)-2-(benzoylamino)-3-(4-methoxy-
phenyl)propenoyl]amino}-5-O-benzyl-2-deoxy-D-glucitol (9f)
Yellow solid; yield: 57%; mp 167–168 °C.
[a]D20 +75 (c 0.10, DMSO).
IR (KBr): 3240, 3058, 2946, 2878, 1646, 1516, 1477, 1338, 1284,
1132, 1092, 1052, 1024, 899, 701 cm–1.
1H NMR (300 MHz, CD3OD): d = 8.77 (s, 1 H), 8.51 (d, J = 6.6 Hz,
1 H), 8.01 (m, 4 H), 7.67–7.36 (m, 10 H), 7.15 (s, 1 H), 4.83–4.78
(m, 2 H), 4.65 (s, 1 H), 4.61 (s, 1 H), 4.46 (s, 1 H), 4.24–4.13 (m, 2
H), 4.06 (dd, J = 9.6, 2.1 Hz, 1 H), 3.94 (dd, J = 9.0, 6.6 Hz, 1 H),
3.76–3.71 (m, 1 H).
13C NMR (75 MHz, CD3OD): d = 172.6, 168.2, 150.9, 149.9, 139.7,
138.5, 134.6, 133.7, 133.6, 132.7, 130.0, 129.7, 129.3, 129.2, 129.1,
126.1, 125.5, 88.6, 82.2, 81.0, 74.2, 73.7, 71.8.
IR (KBr): 3334, 3059, 2949, 2878, 1643, 1622, 1604, 1510, 1482,
1368, 1293, 1176, 1095, 1028, 827, 697 cm–1.
1H NMR (300 MHz, DMSO-d6): d = 9.85 (s, 1 H), 8.27 (d, J = 6.9
Hz, 1 H), 8.00 (d, J = 6.6 Hz, 2 H), 7.59–7.50 (m, 4 H), 7.36–7.29
(m, 5 H), 7.10 (s, 1 H), 6.91 (d, J = 9.0 Hz, 2 H), 4.67–4.63 (m, 2
H), 4.48 (d, J = 11.7 Hz, 2 H), 4.21 (br s, 1 H), 4.12–4.06 (m, 1 H),
3.97 (dd, J = 5.1, 4.2 Hz, 2 H), 3.85–3.78 (m, 2 H), 3.74 (s, 3 H),
3.55 (t, J = 7.5 Hz, 1 H).
HRMS (FAB): m/z [M + H]+ calcd for C28H28N3O5: 486.2029;
found: 486.2037.
13C NMR (75 MHz, DMSO-d6): d = 165.4, 159.4, 138.2, 133.6,
132.3, 131.5, 130.9, 128.6, 128.2, 128.0, 127.8, 127.7, 127.4, 127.3,
126.5, 113.8, 86.8, 79.7, 78.9, 72.5, 71.1, 69.5, 57.3, 55.0.
HRMS (FAB): m/z [M + Na]+ calcd for C30H30N2NaO6: 537.2002;
found: 537.1998.
1,4:3,6-Dianhydro-2-{[(Z)-2-(benzoylamino)-3-(2-furyl)prop-
enoyl]amino}-5-O-benzyl-2-deoxy-D-glucitol (9j)
White solid; yield: 50%; mp 99–100 °C.
[a]D20 +71 (c 0.10, DMSO).
IR (KBr): 3422, 3266, 3060, 2946, 2878, 1651, 1515, 1472, 1364,
1,4:3,6-Dianhydro-2-{[(Z)-2-(benzoylamino)-3-(2-thienyl)prop-
enoyl]amino}-5-O-benzyl-2-deoxy-D-glucitol (9g)
White solid; yield: 60%; mp 157–158 °C.
[a]D20 +60 (c 0.10, DMSO).
1279, 1134, 1091, 1021, 928, 805, 744, 705 cm–1.
1H NMR (300 MHz, DMSO-d6): d = 9.75 (s, 1 H), 8.30 (d, J = 6.9
Hz, 1 H), 8.04 (d, J = 6.9 Hz, 2 H), 7.75 (dd, J = 1.8, 0.6 Hz, 1 H),
7.63–7.50 (m, 3 H), 7.35–7.28 (m, 5 H), 7.04 (s, 1 H), 6.68 (d,
J = 3.6 Hz, 1 H), 6.57 (d, J = 3.0, 1.8 Hz, 1 H), 4.66–4.61 (m, 2 H),
4.52 (d, J = 11.7 Hz, 2 H), 4.22 (br s, 1 H), 4.11–4.04 (m, 1 H),
4.01–3.95 (m, 1 H), 3.84–3.77 (m, 2 H), 3.55 (dd, J = 8.7, 7.5 Hz, 1
H).
13C NMR (75 MHz, DMSO-d6): d = 165.4, 164.6, 149.6, 144.2,
138.1, 133.7, 131.5, 128.2, 128.1, 127.7, 127.4, 127.3, 127.2, 116.6,
113.6, 112.0, 86.6, 79.7, 78.9, 72.4, 71.1, 69.5, 57.3.
IR (KBr): 3392, 3270, 3065, 2874, 1644, 1621, 1580, 1516, 1474,
1341, 1286, 1213, 1113, 1096, 1051, 699 cm–1.
1H NMR (300 MHz, DMSO-d6): d = 9.74 (s, 1 H), 8.26 (d, J = 6.9
Hz, 1 H), 8.06 (d, J = 7.2 Hz, 2 H), 7.64–7.54 (m, 5 H), 7.42 (d,
J = 3.0 Hz, 1 H), 7.40–7.32 (m, 5 H), 7.10 (dd, J = 3.6, 1.5 Hz, 1 H),
4.63 (m, 2 H), 4.48 (d, J = 11.7 Hz, 2 H), 4.23 (br s, 1 H), 4.08 (dd,
J = 6.6, 5.4 Hz, 1 H), 3.97 (m, 1 H), 3.82 (m, 2 H), 3.56 (t, J = 7.5
Hz, 1 H).
HRMS (FAB): m/z [M + H]+ calcd for C27H27N2O6: 475.1869;
found: 475.1873.
13C NMR (75 MHz, DMSO-d6): d = 165.9, 164.6, 138.2, 136.6,
133.8, 131.9, 131.5, 129.9, 128.2, 128.1, 127.9, 127.5, 127.4, 126.8,
126.7, 124.9, 88.8, 79.7, 78.8, 72.4, 71.1, 69.5, 57.3.
HRMS (FAB): m/z [M + Na]+ calcd for C27H26N2NaO5S: 513.1460;
found: 513.1437.
2-{[(Z)-2-(Acetylamino)-3-(2-thienyl)propenoyl]amino}-
1,4:3,6-dianhydro-5-O-benzyl-2-deoxy-D-glucitol (9k)
Pale yellow solid; yield: 50%; mp 78–80 °C.
[a]D20 +85 (c 0.10, DMSO).
1,4:3,6-Dianhydro-2-({(Z)-2-(benzoylamino)-3-[3,4-(methyl-
enedioxy)phenyl]propenoyl}amino)-5-O-benzyl-2-deoxy-D-glu-
citol (9h)
White solid; yield: 60%; mp 140–141 °C.
[a]D20 +53 (c 0.10, DMSO).
IR (KBr): 3249, 3066, 2945, 2875, 1655, 1616, 1526, 1423, 1367,
1269, 1209, 1131, 1088, 1052, 912, 853, 737, 703 cm–1.
1H NMR (300 MHz, DMSO-d6): d = 9.22 (s, 1 H), 8.10 (d, J = 6.9
Hz, 1 H), 7.71 (d, J = 5.1 Hz, 1 H), 7.49 (s, 1 H), 7.42–7.29 (m, 6
H), 7.14 (dd, J = 5.4, 3.6 Hz, 1 H), 4.69–4.64 (m, 2 H), 4.54 (s, 1 H),
4.50–4.46 (m, 1 H), 4.20 (br s, 1 H), 4.11 (q, J = 7.2 Hz, 1 H), 4.01–
3.96 (m, 1 H), 3.86–3.77 (m, 2 H), 3.59–3.54 (m 1 H), 2.05 (s, 3 H).
13C NMR (75 MHz, DMSO-d6): d = 169.9, 164.8, 138.3, 136.7,
131.7, 129.7, 128.1, 127.5, 127.4, 126.9, 126.7, 124.1, 86.7, 79.5,
78.7, 72.2, 70.9, 69.2, 57.0, 22.7.
IR (KBr): 3392, 3234, 2935, 2882, 1641, 1504, 1484, 1447, 1353,
1259, 1097, 1038, 928, 699 cm–1.
1H NMR (300 MHz, DMSO-d6): d = 9.84 (s, 1 H), 8.28 (d, J = 6.6
Hz, 1 H), 8.00 (d, J = 6.9 Hz, 2 H), 7.62–7.50 (m, 3 H), 7.35–7.29
(m, 5 H), 7.16 (d, J = 1.5 Hz, 1 H), 7.10–7.07 (m, 2 H), 6.91 (d,
J = 8.4 Hz, 1 H), 6.00 (s, 2 H), 4.67–4.63 (m, 2 H), 4.49 (d, J = 11.4
Hz, 2 H), 4.20 (br s, 1 H), 4.08 (dd, J = 6.9, 4.8 Hz, 1 H), 4.04–3.95
(m, 1 H), 3.82 (dd, J = 6.6, 2.1 Hz, 2 H), 3.55 (t, J = 7.5 Hz, 1 H).
HRMS (FAB): m/z [M + H]+ calcd for C22H25N2O5S: 429.1484;
found: 429.1487.
1,4:3,6-Dianhydro-2-{[(Z)-2-(benzoylamino)-3-(1-benzo-
thiophen-2-yl)propenoyl]amino}-5-O-benzyl-2-deoxy-D-gluci-
tol (9l)
White solid; yield: 40%; mp 180–182 °C.
[a]D20 +64 (c 0.10, DMSO).
13C NMR (75 MHz, DMSO-d6): d = 165.7, 165.4, 147.5, 147.3,
138.2, 133.6, 131.6, 128.6, 128.3, 128.2, 128.1, 127.8, 127.5, 127.4,
127.3, 124.8, 108.3, 108.2, 101.2, 86.8, 79.8, 78.9, 72.5, 71.2, 69.5,
57.4.
HRMS (FAB): m/z [M + Na]+ calcd for C30H28N2NaO7: 551.1794;
found: 551.1785.
IR (KBr): 3429, 3267, 3059, 2938, 1651, 1621, 1538, 1471, 1331,
1277, 1140, 1093, 1093, 1045, 994, 893, 752, 698 cm–1.
1,4:3,6-Dianhydro-2-{[(Z)-2-(benzoylamino)-3-(3-pyridyl)pro-
penoyl]amino}-5-O-benzyl-2-deoxy-D-glucitol (9i)
White solid; yield: 62%; mp 161–162 °C.
[a]D20 +72 (c 0.10, DMSO).
1H NMR (300 MHz, DMSO-d6): d = 9.94 (s, 1 H), 8.46 (d, J = 6.6
Hz, 1 H), 8.11 (d, J = 6.9 Hz, 2 H), 7.87 (dd, J = 7.5, 5.1 Hz, 2 H),
7.85 (s, 1 H), 7.75–7.57 (m, 4 H), 7.34–7.28 (m, 6 H), 4.67–4.63 (m,
2 H), 4.52 (d, J = 11.4 Hz, 2 H), 4.24 (br s, 1 H), 4.13–4.06 (m, 1
Synthesis 2009, No. 4, 620–626 © Thieme Stuttgart · New York