Molecules 2005, 10
Penta-O-(3-bromo)benzoyl-α-D-glucopyranose: H-NMR δ (ppm): 4.53 (dd, J6,6’ = 12.48 Hz, J5,6
1331
1
=
4.73 Hz, 1H, H-6), 4.59 – 4.63 (m, 2H, H-5, H-6’), 5.65 (dd, J2,3 = 10.16 Hz, J1,2 = 3.92 Hz, 1H, H-2),
5.77 (dd, J3,4 = 9.93 Hz, J4,5 = 9.92 Hz, 1H, H-4), 6.20 (dd, J3,4 = 9.97 Hz, J2,3 = 9.91 Hz, 1H, H-3),
6.82 (d, J1,2 = 3.74 Hz, 1H, H-1), 7.22 (t, J = 7.90 Hz, 2H), 7.26 (t, J = 6.42 Hz, 2H), 7.32 (t, J = 7.87
Hz, 1H), 7.46 (t, J = 7.90 Hz, 1H), 7.62 (td, J1 = 8.17 Hz, J2 = 0.92 Hz, 2H), 7.66 (dt, J1 = 7.99 Hz, J2 =
0.94 Hz, 1H), 7.69 (dt, J1 = 7.91 Hz, J2 = 0.96 Hz, 1H), 7.78 – 7.83 (m, 3H), 7.87 (d, J = 7.81 Hz, 1H),
7.95 (d, J = 7.78 Hz, 1H), 7.98 (t, J = 1.62 Hz, 1H), 8.01 (t, J = 1.57 Hz, 1H), 8.10 (td, J1 = 7.81 Hz, J2
13
= 1.60 Hz, 2H), 8.25 (t, J = 1.60 Hz, 1H); C-NMR δ (ppm): 62.88 (C-6), 79.08 (C-4), 70.23 (C-5),
70.55 (C-2), 70.78 (C-3), 90.28 (C-1), 122.63, 122.98, 128.27, 128.44, 130.10, 130.46, 131.22, 132.74,
133.00, 136.28, 136.61, 136.68, 136.74, 137.08, 137.65, 163.24, 163.84, 163.93, 164.53, 164.68;
HRMS calc. for C41H27Br5O11Na: 1118.7307, found: 1118.7327.
1
Penta-O-(3-bromo)benzoyl-α-D-mannopyranose: H-NMR δ (ppm): 4.55 – 4.59 (m, 2H, H-5, H-6),
4.66 (dd, J6,6’ = 12.07 Hz, J5,6’ = 2.72 Hz, 1H, H-6’), 5.89 (dd, J2,3 = 3.11 Hz, J1,2 = 1.97 Hz, 1H, H-2),
5.97 (dd, J3,4 = 10.13 Hz, J2,3 = 3.32 Hz, 1H, H-3), 6.07 (dd, J3,4 = 10.05 Hz, J4,5 = 9.98 Hz, 1H, H-4),
6.59 (d, J1,2 = 1.52 Hz, 1H, H-1), 7.20 (t, J = 7.89 Hz, 1H), 7.26 (t, J = 8.15 Hz, 1H), 7.28 (t, J = 7.99
Hz, 2H), 7.33 (t, J = 7.90 Hz, 1H), 7.46 (t, J = 7.87 Hz, 1H), 7.62 (dd, J1 = 7.95 Hz, J2 = 0.87 Hz, 1H),
7.65 (dd, J1 = 7.97 Hz, J2 = 0.86 Hz, 1H), 7.68 (dd, J1 = 7.90 Hz, J2 = 0.86 Hz, 1H); 13C-NMR δ (ppm):
62.86 (C-6), 66.76 (C-4), 69.57 (C-2), 70.13 (C-3), 70.88 (C-5), 91.71 (C-1). 122.58, 122.64, 122.92,
128.14, 128.19, 128.40, 128.62, 130.06, 130.39, 132.71, 133.02, 133.07, 136.19, 136.59, 136.71,
136.89, 137.18, 162.60, 164.00 (2C), 164.21, 164.64; HRMS calc. for C41H27Br5O11Na: 1118.7307,
found: 1118.7250.
Octa-O-(3-bromo)benzoyl-α-lactose: 1H-NMR δ (ppm): 3.80 – 3.84 (m, 1H, H-6, Gal), 3.88 (dd, J6,6’
=
11.26 Hz, J5,6’ = 6.18 Hz, 1H, H-6’, Gal), 4.00 (s, br, 1H, H-5, Gal), 4.30 – 4.32 (br, 2H, H-4, Glc, H-5,
Glc), 4.56 (br, 2H, H-6, Glc, H-6’, Glc), 5.00 (d, J1,2 = 5.86 Hz, 1H, H-1, Gal), 5.46 (dd, J2,3 = 9.92 Hz,
J3,4 = 2.71 Hz, 1H, H-3, Gal), 5.60 (dd, J2,3 = 10.11 Hz, J1,2 = 3.75 Hz, 1H, H-2, Glc), 5.69 (dd, J2,3
=
10.12 Hz, J1,2 = 7.93 Hz, 1H, H-2, Gal), 5.75 (d, J3,4 = 2.42 Hz, 1H, H-4, Gal), 6.13 (dd, J2,3 = 9.58 Hz,
J3,4 = 8.57 Hz, 1H, H-3, Glc), 6.73 (d, J1,2 = 3.64 Hz, 1H, H-1, Glu), 7.12 – 7.20 (m, 4H), 7.30 – 7.33
(m, 2H), 7.41 – 7.44 (m, 2H), 7.52 (t, J = 7.83 Hz, 1H), 7.56 (t, J = 7.81 Hz, 2H), 7.60 (d, J = 7.03 Hz,
2H), 7.69 (t, J = 7.91 Hz, 2H), 7.78 (t, J = 7.75 Hz, 3H), 7.81 (s, 1H), 7.86 (t, J = 8.35 Hz, 2H), 7.90 (t,
J = 5.20 Hz, 2H), 7.97 (s, 1H), 7.99 (d, J = 7.83 Hz, 1H), 8.04 – 8.09 (m, 5H), 8.18 (d, J = 1.47 Hz,
13
2H); C-NMR δ (ppm): 60.89 (C-6, Gal), 62.05 (C-6, Glc), 67.62 (C-4, Gal), 70.33 (C-2, Gal, C-2,
Glc), 70.86 (C-3, Glc), 71.11 (C-5, Glc, C-5, Gal), 71.89 (C-3, Gal), 75.68 (C-4, Glc), 90.07 (C-1,
Glc), 101.00 (C-1, Gal), 122.48, 122.56, 122.61, 122.68, 122.87, 128.10, 128.17, 128.33, 128.37,
129.92, 130.08, 130.19, 130.38, 130.50, 130.97, 131.11, 132.44, 132.64, 132.77, 132.92, 136.36,
136.39, 136.46, 136.57, 136.84, 136.97, 163.23, 163.58, 163.97, 164.38; HRMS calc. for
C68H46Br8O19Na: 1828.5917, found: 1828.3177.
References and Notes