ORDER
REPRINTS
538
Mishra et al.
1
2
5
22.6, 120.2, 119.4 (Ar-C), 112.2 [C(CH ) ], 111.6, 111.4 (Ar-C), 105.3 (C-1), 84.3 (C-
2
3
), 81.5 (C-4), 80.7 (C-3), 61.5 (–OCH CH ), 58.10 (–OCH ), 56.3, 56.3 (Ar–OCH ),
2
3
3
3
3.80 (C-5), 35.9 (C-6), 27.1 and 26.5 [C(CH ) ], 14.6 (CH ). Anal. Calcd for
2
3
3
C H N O : C, 62.36; H, 6.81; N, 5.01. Found: C, 62.48; H, 6.44; N, 4.81.
29 38 2 9
Ethyl 5[N’-Benzyl-N-(3,4-dimethoxybenzyl)ureido]-5,6-dideoxy-1,2,-O-isopro-
pyli-dene-3-O-methyl-b-L-ido-heptofuranuronate (15): Colourless foam, yield 1.23 g
2
0
(
96 %), R 0.40 (3:2 hexane/ethyl acetate), [a]
À23.29 (c 0.85,CHCl ). MS (FAB):
f
D
3
+
m/z 573 (M + H) . IR (Neat) n : 3404, 2989, 2368, 1730, 1646, 1519, 1259, 856,
755, 599 cm . H NMR (CDCl ): d 7.27–7.16 (m, 3H, ArH), 7.11–7.09 (m, 2H,
ArH), 6.77–6.74 (m, 3H, ArH), 5.86 (d, J = 3.7 Hz, 1H, H-1), 5.13 (br s, 1H, NH), 4.58 (d,
max
À1
1
3
J = 3.7 Hz, 1H, H-2), 4.49–4.28 (m, 5H, –NCH , –NHCH and H-5), 4.14–4.04 (m, 3H,
2
2
H-4, and –OCH ), 3.83 and 3.81 (2 s, each 3H, ArOCH ), 3.58 (s, 1H, H-3), 3.35 (s, 3H,
2
3
OCH ), 2.94-2.86 (m, 1H, H-6 ), 2.44 (dd, J = 15.3 and 3.1 Hz, 1H, H-6 ), 1.35 and 1.29
3
A
B
1
3
[
2 s, each 3H, C(CH ) ], 1.24 (t, J = 7.3 Hz, 3H, OCH CH ). C NMR (CDCl ): d 171.7
3
2
2
3
3
(
1
C = O), 159.3 (NHC = O), 149.9, 148.6, 140.10, 131.8 128.9, 128.7, 127.9, 127.8 127.5,
27.4, 127.1, 118.9, 112.2 (Ar-C), 112.0 [C(CH ) ], 111.4, 111.2, 110.8 (Ar-C), 105.1
3
2
(
(
C-1), 84.1 (C-2), 81.5 (C-4), 80.1 (C-3), 61.2 (–OCH CH ), 57.7 (–OCH ), 56.3, 56.2
2 3 3
Ar–OCH ), 45.4 (–NCH ), 36.7 (C-1), 27.1 and 26.8 [C(CH ) ] 14.6 (CH ). Anal.
3
2
3 2
3
Calcd for C H N O : C, 62.93; H, 6.99; N, 4.89. Found: C, 61.8; H, 7.08; N, 4.63.
30 40 2 9
Ethyl 3-O-Benzyl-5-[N-(2-chlorobenzyl)-N’-phenylureido]-5,6-dideoxy-1,2,-O-
isopropylidene-b-L-ido-heptofuranuronate (16): Colourless foam, yield 1.1 g (90 %),
2
0
R 0.45 (3:2 hexane/ethyl acetate), [a]
À12.5 (c 0.2,CHCl ). MS (FAB): m/z 610
f
D
3
+
(
M + H) . IR (Neat) n : 3343, 2995, 2934, 2363, 1729, 1834, 1524, 1450, 1378,
174, 1081, 1023, 853, 758 cm . H NMR (CDCl ): d 7.7 (br s, 1H, NH), 7.46–7.43
max
À1
1
1
3
(m, 2H, ArH), 7.34–7.15 (m, 10H, ArH), 7.00–6.95 (m, 2H, ArH), 5.95 (d, J = 3.6 Hz,
1
1
H, H-1), 4.86–4.54 (m, 5H, –OCH Ph, H-2, -NCH and H-5), 4.40 (d, J = 11.9 Hz,
A 2
H, –OCH ), 4.34–4.30 (m, 1H, H-4), 4.05 (q, J = 7.1 Hz, 2H, –OCH ), 3.77 (s, 1H,
B
2
H-3), 2.56–2.43 (m, 1H, H-6 ), 2.00 (dd, J = 16.5 and 2.4 Hz, 1H, H-6 ), 1.55 and
A
B
1
3
1
.37 [2 s, each 3H, C(CH ) ], 1.25 (t, J = 7.14 Hz, 3H, –OCH CH ). C NMR
3 2 2 3
(
CDCl ): d 171.8 (C = O), 157.7 (NHC = O), 140.1, 137.0, 136.7, 132.6, 129.7, 129.6,
3
1
8
3
6
29.3, 129.1, 128.8 128.6, 127.5, 123.6, 120.2 (Ar-C), 111.9 [C(CH ) ], 105.2 (C-1),
2.2 (C-2), 80.9 (C-4), 79.5 (C-3), 71.8 (–OCH Ph), 61.5 (–OCH CH ), 52.5 (–NCH ),
3 2
2
2
3
2
4.8 (C-6), 27.2 and 26.8 [C(CH ) ], 14.5 (CH ). Anal. Calcd for C H N O Cl : C,
33 37 2 7
3
2
3
5.07; H, 6.08; N,4.60. Found: C, 65.36; H, 6.32; N, 4.34.
Ethyl 3-O-Benzyl-5-[N’-(4-chlorophenyl)-N-(4-methoxybenzyl)ureido]-5,6-
dideoxy-1,2-O-isopropylidene-b-L-ido-heptofuranuronate (17): Colourless foam,
2
0
yield 1.25g (%), R 0.40 (3:2 hexane/ethyl acetate) [a]
À13.81 (c 0.1375,CHCl ).
f
D
3
+
MS (FAB): m/z 640 (M + H) . IR (Neat) n : 2992, 2312, 1729, 1682, 1597, 1426,
1211, 870, 756 cm . H NMR (CDCl ): d 7.59 (bs, 1H, NH), 7.30–7.23 (m, 8H,
ArH), 7.16 (s, 3H, ArH), 6.82(d, J = 8.54 Hz, 2H, ArH), 5.96 (d, J = 3.7 Hz, 1H, H-1),
max
À1
1
3
4
H-2), 4.56-4.37 (m, 4H, N-CH , H-4 and H-5), 4.08 (q, J = 7.1 Hz, 2H,-OCH ), 3.76
.72 and 4.40 (2 d, J = 11.7 Hz, each 1H, OCH and OCH ), 4.66 (d, J = 3.7 Hz, 1H,
A
B
2
2
(s, 4H, –OCH and H-3), 2.84–2.77 (m, 1H, H-6 ), 2.03 (dd, J = 16.7 and 2.2 Hz, 1H,
H-6 ), 1.40, 1.31 [2 s, each 3H, C(CH ) ], 1.23 (t, J = 7.14 Hz, 3H, –OCH CH ).
3
A
1
3
C
B
3 2
2
3