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ꢀ
25
D
25
D
Data for 5d. Solid; yield 77% (520 mg); mp 105–107 C; [a]
Data for 5h. Yellow oil; yield 72% (469 mg); [a]
+69 (c 1.0,
+
1
98 (c 1.0, CHCl ); IR (KBr): 3021, 2268, 1633, 1566, 1454, 1219, CHCl ); IR (neat): 3018, 2363, 1748, 1636, 1553, 1466, 1405,
3
3
ꢁ1
1
ꢁ1
1
081, 758, cm ; H NMR (400 MHz, CDCl
3
): d 7.98 (d, J ¼ 8.9 1218, 1085, 770, 668 cm ; H NMR (400 MHz, CDCl
3
): d 8.42 (s,
Hz, 2H), 7.69 (s, 1H), 7.49–7.44 (m, 2H), 7.35–7.25 (m, 2H), 6.92 1H), 8.23 (d, J ¼ 8.5 Hz, 1H), 7.97 (d, J ¼ 8.4 Hz, 2H), 7.91 (d, J ¼
d, J ¼ 8.9 Hz, 2H), 5.34 (d, J ¼ 3.3 Hz, 1H), 5.24 (dd, J ¼ 7.9, 10.5 9.1 Hz, 1H), 7.82 (d, J ¼ 8.0 Hz, 1H), 7.67–7.63 (m, 1H), 7.54–7.49
Hz, 1H), 4.98 (dd, J ¼ 3.5, 10.5 Hz, 1H), 4.72 (dd, J ¼ 1.4, 15.3 Hz, (m, 1H), 7.40 (d, J ¼ 9.1 Hz, 1H), 7.26 (d, J ¼ 8.1 Hz, 2H), 5.39–
(
1
H), 4.57 (d, J ¼ 7.9 Hz, 1H), 4.45 (dd, J ¼ 1.3, 15.3 Hz, 1H), 4.07 5.36 (m, 2H), 5.07 (t, J ¼ 9.7 Hz, 1H), 4.86 (br s, 1H), 4.68 (dd, J ¼
(d, J ¼ 6.2 Hz, 1H), 3.88–3.85 (m, 1H), 3.77 (s, 3H), 2.08 (s, 3H), 1.3, 15.3 Hz, 1H), 4.39 (dd, J ¼ 1.2, 15.3 Hz, 1H), 3.95–3.88 (m,
1
3
1.98 (s, 3H), 1.95 (s, 3H), 1.92 (s, 3H); C NMR (100 MHz, 1H), 2.33 (s, 3H), 2.10 (s, 3H), 1.99 (s, 3H), 1.98 (s, 3H), 1.18 (d,
1
3
CDCl
3
): d 170.4, 170.2, 169.9, 169.7, 162.9, 155.8, 151.9, 137.4, J ¼ 6.3 Hz, 3H); C NMR (100 MHz, CDCl
3
): d 170.3, 170.2,
133.8, 131.9, 129.8 (2C), 128.3, 126.1, 125.9, 119.2, 116.3, 113.9 169.9, 156.1, 151.7, 143.4, 138.9, 133.4, 133.3, 130.7, 129.3 (2C),
(
2
2C), 101.4, 70.9, 70.7, 68.9, 67.0, 66.3, 61.2, 55.6, 20.8, 20.6 (2C), 128.9, 128.8, 128.6, 127.6 (2C), 126.8, 125.1, 121.8, 115.8, 113.8,
+
0.5; ESI-MS: m/z 676.0 [M + H] . Anal. calcd for C31
H
33NO14
S
97.3, 70.9, 69.8, 69.1, 67.2, 64.1, 21.6, 20.9, 20.8 (2C), 17.4; ESI-
+
(675.16): C, 55.11; H, 4.92. Found: C, 55.01; H, 5.03%.
MS: m/z 651.9 [M + H] . Anal. calcd for C H NO S (651.17): C,
3
3
33
11
ꢀ
25
D
Data for 5e. Solid; yield 88% (529 mg); mp 85–87 C; [a] +77 60.82; H, 5.10. Found: C, 60.71; H, 5.22%.
ꢀ
(c 1.0, CHCl ); IR (KBr): 3021, 2402, 1632, 1568, 1485, 1405,
Data for 5i. White solid; yield 73% (526 mg); mp 120–122 C;
3
ꢁ1
1
25
D
1
218, 1083, 927, 668 cm ; H NMR (400 MHz, CDCl
3
): d 7.92 (d, [a]
ꢁ78 (c 1.0, CHCl
3
); IR (KBr): 3020, 2328, 1629, 1564, 1216,
ꢁ
1
1
J ¼ 8.2 Hz, 2H), 7.72 (s, 1H), 7.49–7.46 (m, 2H), 7.33–7.23 (m, 1159, 1086, 1020, 909, 759, 677 cm
; H NMR (400 MHz,
4
4
1
H), 5.29–5.26 (m, 2H), 5.03 (t, J ¼ 9.5 Hz, 1H), 4.79 (br s, 1H), CDCl ): d 8.38–8.31 (m, 2H), 7.94 (d, J ¼ 9.0 Hz, 2H), 7.76 (s, 1H),
3
.59 (d, J ¼ 15.2 Hz, 1H), 4.31 (d, J ¼ 15.3 Hz, 1H), 3.91–3.84 (m, 7.51 (d, J ¼ 9.0 Hz, 1H), 6.95 (d, J ¼ 9.0 Hz, 2H), 5.35 (d, J ¼ 3.4
H), 2.32 (s, 3H), 2.08 (s, 3H), 1.98 (s, 3H), 1.94 (s, 3H), 1.16 (d, Hz, 1H), 5.24 (dd, J ¼ 8.0, 10.4 Hz, 1H), 4.99 (dd, J ¼ 3.4, 10.5 Hz,
1
3
J ¼ 6.3 Hz, 3H); C NMR (100 MHz, CDCl ): d 170.2, 170.1, 1H), 4.70 (dd, J ¼ 1.4, 15.3 Hz, 1H), 4.56 (d, J ¼ 8.0 Hz, 1H), 4.42
3
1
1
6
69.9, 156.1, 152.0, 143.5, 138.6, 137.5, 132.0, 129.3 (2C), 128.4, (dd, J ¼ 1.3, 15.5 Hz, 1H), 4.07 (t, J ¼ 6.3 Hz, 2H), 3.87 (t, J ¼ 6.8
27.6 (2C),125.9, 125.8, 119.0, 116.3, 97.4, 70.8, 69.6, 69.1, 66.9, Hz, 1H), 3.80 (s, 3H), 2.10 (s, 3H), 1.99 (s, 3H), 1.96 (s, 3H), 1.94
+
13
3.9, 21.5, 20.9, 20.8, 20.7, 17.4; ESI-MS: m/z 602.0 [M + H] . (s, 3H); C NMR (100 MHz, CDCl
3
): d 170.4, 170.2, 170.3, 169.7,
Anal. calcd for C29
H
31NO11S (601.16): C, 57.90; H, 5.19. Found: 163.3, 154.8, 153.9, 144.9, 135.5, 132.7, 129.7 (2C), 128.9, 126.4,
C, 57.76; H, 5.31%.
123.9, 119.5, 117.7, 114.1 (2C), 101.2, 70.9, 70.6, 68.8, 66.9, 65.7,
+57 61.1, 55.7, 20.8, 20.7 (2C), 20.6; ESI-MS: m/z 721.0 [M + H] . Anal.
2
5
+
Data for 5f. Light yellow syrup; yield 69% (440 mg); [a]
D
(
1
3 32 2
c 1.0, CHCl ); IR (neat): 3020, 1744,1634, 1553, 1515, 1466, calcd for C31H N O16S (720.14): C, 51.67; H, 4.48. Found: C,
ꢁ1 1
218, 1048, 770, 667 cm ; H NMR (400 MHz, CDCl ): d 8.66 (d, 51.58; H, 4.63%.
3
2
5
J ¼ 8.6 Hz, 1H), 8.47 (d, J ¼ 7.4 Hz, 1H), 7.95 (d, J ¼ 8.5 Hz, 1H),
Data for 5j. White foam; yield 72% (510 mg); [a] ꢁ44 (c 1.0,
D
7
.78 (d, J ¼ 8.1 Hz, 1H), 7.66 (s, 1H), 7.55–7.50 (m, 2H), 7.46–7.36 CHCl ); IR (neat): 3020, 2326, 1633, 1560, 1457, 1383, 1318,
3
ꢁ1 1
(
(
1
2
m, 3H), 7.21–7.17 (m, 1H), 7.12 (d, J ¼ 8.2 Hz, 1H), 5.28–5.24 1255, 1214, 1160, 1086, 1070, 1002, 905, 671 cm ; H NMR (400
m, 2H), 5.02 (t, J ¼ 9.6 Hz, 1H), 4.75 (br s, 1H), 4.56 (dd, J ¼ 1.3, MHz, CDCl
3
): d 8.55 (s, 1H), 8.34 (d, J ¼ 8.4 Hz, 1H), 7.97–7.93
5.2 Hz, 1H), 4.28 (dd, J ¼ 1.3, 15.2 Hz, 1H), 3.84–3.77 (m, 1H), (m, 3H), 7.85 (d, J ¼ 8.4 Hz, 1H), 7.67 (t, J ¼ 7.4 Hz, 1H), 7.54 (t,
1
3
.06 (s, 3H), 1.96 (s, 3H), 1.93 (s, 3H), 1.11 (d, J ¼ 6.4 Hz, 3H);
): d 170.2, 170.1, 169.9, 156.4, 151.9, 5.38–5.31 (m, 2H), 5.03 (dd, J ¼ 3.3, 10.5 Hz, 1H), 4.87 (d, J ¼
37.8, 137.4, 134.1, 134.0, 132.0, 128.7, 128.6, 128.5, 128.3, 15.5 Hz, 1H), 4.61 (d, J ¼ 8.1 Hz, 1H), 4.49 (d, J ¼ 15.4 Hz, 1H),
C
J ¼ 7.3 Hz, 1H), 7.46 (d, J ¼ 9.0 Hz, 1H), 7.26 (d, J ¼ 7.8 Hz, 2H),
NMR (100 MHz, CDCl
3
1
1
6
27.9, 126.7, 125.9, 125.7, 125.6, 124.1, 118.9, 116.2, 97.3, 70.8, 4.11–4.09 (m, 2H), 3.89 (t, J ¼ 6.5 Hz, 1H), 2.34 (s, 3H), 2.11 (s,
1
3
9.5, 69.1, 66.9, 63.8, 20.9, 20.8, 20.7, 17.3; ESI-MS: m/z 638.0 3H), 1.96 (s, 6H), 1.94 (s, 3H); C NMR (100 MHz, CDCl ): d
3
+
[M + H] . Anal. calcd for C32
H
31NO11S (637.16): C, 60.27; H, 4.90. 170.4, 170.2, 170.0 (2C), 155.9, 151.6, 143.4, 138.9, 133.6, 133.3,
130.8, 129.3 (2C), 128.9, 128.8, 128.7, 127.6 (2C), 126.8, 125.5,
Found: C, 60.16; H, 5.05%.
ꢀ
25
Data for 5g. Solid; yield 70% (463 mg); mp 90–92 C; [a]
c 1.0, CHCl ); IR (KBr): 3017, 2363, 1659, 1610, 1512, 1436, 21.6, 20.9, 20.7 (2C), 20.5; ESI-MS: m/z 710.0 [M + H] . Anal.
246, 1091, 759, 601 cm ; H NMR (400 MHz, CDCl
dd, J ¼ 2.8, 9.0 Hz, 1H), 7.92 (d, J ¼ 9.1 Hz, 2H), 7.81 (s, 1H), 59.11; H, 5.15%.
.73 (d, J ¼ 9.0 Hz, 1H), 7.49 (d, J ¼ 9.1 Hz, 1H), 6.84 (d, J ¼ 9.1 Data for 5k. Light yellow syrup; yield 72% (486 mg); [a]D +54
Hz, 2H), 5.29–5.26 (m, 2H), 5.03 (t, J ¼ 9.6 Hz, 1H), 4.80 (br s, (c 1.0, CHCl ); IR (neat): 3020, 2403,1634, 1549, 1515, 1465,
D
+67 121.9, 115.9, 114.2, 101.6, 71.0, 70.5, 69.2, 67, 3, 67.0, 66.6, 61.3,
+
(
1
(
7
3
ꢁ
1 1
3
): d 8.31 calcd for C35H35NO13S (709.18): C, 59.23; H, 4.97. Found: C,
2
5
3
ꢁ
1 1
1
H), 4.56 (d, J ¼ 15.4 Hz, 1H), 4.31 (d, J ¼ 15.5 Hz, 1H), 3.87–3.82 1218, 1152, 1042, 759, 678 cm ; H NMR (400 MHz, CDCl
3
): d
(
(
1
1
6
m, 1H), 3.79 (s, 3H), 2.08 (s, 3H), 1.98 (s, 3H), 1.94 (s, 3H), 1.16 7.93 (d, J ¼ 7.6 Hz, 2H), 7.68 (s, 1H), 7.50–7.36 (m, 3H), 7.29–7.24
1
3
d, J ¼ 6.3 Hz, 3H); C NMR (100 MHz, CDCl
3
): d 170.2 (2C), (m, 3H), 5.31 (d, J ¼ 3.1 Hz, 1H), 5.12 (t, J ¼ 9.9 Hz, 1H), 4.90 (dd,
69.9, 163.3, 154.8, 154.1, 144.8, 135.6, 132.5, 129.7, 128.7, J ¼ 3.3, 9.9 Hz, 1H), 4.64 (d, J ¼ 10.0 Hz, 1H), 3.97–3.95 (m, 2H),
28.4, 126.5, 124.0, 119.3, 117.7, 114.1 (2C), 97.5, 70.7, 69.5, 3.78–3.66 (m, 3H), 2.36 (s, 3H), 2.07 (s, 3H), 1.98 (s, 3H), 1.91 (s,
1
3
9.1, 67.1, 63.8, 55.7, 20.8, 20.7 (2C), 17.4; ESI-MS: m/z 685.1 6H); C NMR (100 MHz, CDCl ): d 170.3, 170.2, 169.9, 169.7,
3
+
[M + Na] . Anal. calcd for C H N O S (662.14): C, 52.57; H, 157.6, 152.1, 143.5, 139.5, 138.9, 132.1, 129.4 (2C), 127.9, 127.5
2
9
30 2 14
4.56. Found: C, 52.43; H, 4.66%.
(2C), 125.9, 119.2, 116.5 (2C), 84.5, 74.3, 71.7, 67.4, 67.2, 61.3,
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RSC Adv., 2014, 4, 5803–5814 | 5809