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Received: 31st July 2002; Com. 02/1979
§
Selected 1H NMR data (500 MHz, D2O).
3-Aminopropyl 2-acetamido-2-deoxy-4-O-(b-D-galactopyranosyl)-6-
3-Aminopropyl 2-acetamido-2-deoxy-3-O-sulfo-b-D-galactopyranoside
(sodium salt) 10: 1.97 (m, 2H, CCH2C), 2.06 (s, 3H, NAc), 3.11 (m, 2H,
CH2N), 3.74–3.79 (m, 1H, OCH), 3.76 (dd, 1H, H-5, J5,6a 4.6 Hz, J5,6b
7.6 Hz), 3.81 (dd, 1H, H-6a, J5,6a 4.6 Hz, J6a,6b 11.7 Hz), 3.84 (dd, 1H,
H-6b, J5,6b 7.6 Hz, J6a,6b 11.7 Hz), 4.03–4.08 (m, 1H, OCH), 4.07 (dd,
O-sulfo-b-D-glucopyranoside (sodium salt)
15: 1.94 (m, 2H, CCH C),
2.03 (s, 3H, NAc), 3.09 (m, 2H, CH2N), 3.52 (dd, 1H, H-2', J1',2' 7.82Hz,
J2',3' 10 Hz), 3.66 (dd, 1H, H-3', J2',3' 10 Hz, J3',4' 3.4 Hz), 3.68–3.80 (m,
8H, OCH, H-2, H-3, H-4, H-5, H-5', H-6'a and H-6'b), 3.91 (br. d, 1H,
H-4', J3',4' 3.4 Hz, J4',5' < 1 Hz), 3.98 (m, 1H, OCH), 4.32 (dd, 1H, H-6a,
J6a,6b 11 Hz, J5,6a 4 Hz), 4.41 (dd, 1H, H-6b, J6a,6b 11 Hz, J5,6b 1.7 Hz),
4.51 (d, 1H, H-1', J1',2' 7.8 Hz), 4.54 (d, 1H, H-1, J1,2 8.1 Hz).
1H, H-2, J1,2 8.6 Hz, J2,3 11 Hz), 4.27 (br. d, 1H, H-4, J3,4 3 Hz, J4,5
<
< 1 Hz), 4.43 (dd, 1H, H-3, J2,3 11 Hz, J3,4 3 Hz), 4.61 (d, 1H, H-1, J1,2
8.6 Hz).
3-Aminopropyl 2-acetamido-2-deoxy-4-O-(6-O-sulfo-b-D-galacto-
pyranosyl)-b-D-glucopyranoside (sodium salt) 16: 1.95 (m, 2H, CCH2C),
2.07 (s, 3H, NAc), 3.09 (m, 2H, CH2N), 3.57 (dd, 1H, H-2', J1',2' 8.1 Hz,
J2',3' 10 Hz), 3.65 (ddd, 1H, H-5, J4,5 9.5 Hz, J5,6a 5.1 Hz, J5,6b 2.2 Hz),
3.71 (dd, 1H, H-3', J2',3' 10 Hz, J3',4' 3.4 Hz), 3.70–3.78 (m, 4H, H-2, H-3,
H-4 and OCH), 3.85 (dd, 1H, H-6a, J6a,6b 11.2 Hz, J5,6a 5.1 Hz) 3.98–4.07
(m, 4H, H-4', H-5', H-6b and OCH), 4.22 (m, 2H, H-6'a and H-6'b),
4.53 (d, 1H, H-1, J1,2 7.8 Hz), 4.54 (d, 1H, H-1', J1',2' 8.1 Hz).
3-Aminopropyl 2-acetamido-2-deoxy-3-O-(3-O-sulfo-b-D-galacto-
pyranosyl)-b-D-glucopyranoside (sodium salt) 17: 1.87 (m, 2H, CCH2C),
2.05 (s, 3H, NAc), 3.10 (m, 2H, CH2N), 3.51 (ddd, 1H, H-5, J4,5 9.7 Hz,
J5,6a 5.4 Hz, J5,6b 2.2 Hz), 3.57 (dd, 1H, H-4, J3,4 8.1 Hz, J4,5 9.7 Hz),
3.67 (m, 1H, OCH), 3.68 (dd, 1H, H-2', J1',2' 8.1 Hz, J2,3 9.5 Hz), 3.78
(dd, 1H, H-6a, J5,6a 5.4 Hz, J5,6a,6b 12.5 Hz), 3.77–3.88 (m, 4H, H-3, H-4,
H-6'a and H-6'b), 3.84 (dd, 1H, H-2, J1',2' 7.8 Hz, J2',3' 9.5 Hz), 3.94
(m, 1H, H-6b), 3.96 (m, 1H, OCH), 4.31 (br. d, 1H, H-4', J3',4' 3.4 Hz,
J4',5' < 1 Hz), 4.33 (dd, 1H, H-3', J2',3' 9.5 Hz, J3',4' 3.4 Hz), 4.565 (d, 1H,
H-1, J1,2 7.8 Hz), 4.57 (d, 1H, H-1', J1',2' 8.1 Hz).
3-Aminopropyl 2-acetamido-2-deoxy-3-O-(3-O-sulfo-b-D-galacto-
pyranosyl)-a-D-galactopyranoside (pyridinium salt) 18: 1.95 (m, 2H,
CCH2C), 2.01 (s, 3H, NAc), 3.12 (m, 2H, CH2N), 3.56 (m, 1H, OCH),
3.65 (dd, 1H, H-2', J1',2' 7.8 Hz, J2',3' 8.8 Hz), 3.68–3.85 (m, 6H, OCH,
H-5', H-6a, H-6b, H-6'a and H-6'b), 3.96 (m, 1H, H-5), 4.03 (dd, 1H, H-3,
J2,3 11.1 Hz, J3,4 2.9 Hz), 4.25 (br. d, 1H, H-4, J3,4 3 Hz, J4,5 < 1 Hz),
4.27 (m, 2H, H-3', H-4'), 4.33 (dd, 1H, H-2, J1,2 3.7 Hz, J2,3 11.1 Hz),
4.56 (d, 1H, H-1', J1',2' 7.8 Hz), 4.90 (d, 1H, H-1, J1,2 3.7 Hz), 8.09 (m,
2H, Py), 8.63 (m, 1H, Py), 7.79 (m, 2H, Py).
3-Aminopropyl 2-acetamido-2-deoxy-4-O-sulfo-b-D-galactopyranoside
(sodium salt) 11: 1.98 (m, 2H, CCH2C), 2.07 (s, 3H, NAc), 3.13 (m, 2H,
CH2N), 3.76 (m, 1H, OCH), 3.81–3.87 (m, 3H, H-5, H-6a and H-6b),
3.9 (dd, 1H, H-3, J2,3 11 Hz, J3,4 2.7 Hz), 3.93 (dd, 1H, H-2, J1,2 7.6 Hz,
J2,3 11 Hz), 4.06 (m, 1H, OCH), 4.51 (d, 1H, H-1, J1,2 7.6 Hz), 4.72
(br. d, 1H, H-4, J3,4 2.7 Hz, J4,5 < 1 Hz).
3-Trifluoroacetamidopropyl
2-acetamido-2-deoxy-6-O-sulfo-a-D-
galactopyranoside (triethylammonium salt) 12: 1.30 (t, 9H, NCH2Me,
J 7.3 Hz), 1.92 (m, 2H, CCH2C), 2.07 (s, 3H, NAc), 3.21 (q, 6H,
NCH2Me, J 7.3 Hz), 3.34 (m, 1H, CHN), 3.48–3.55 (m, 2H, CHN and
OCH), 3.80 (m, 1H, OCH), 3.95 (dd, 1H, H-3, J2,3 11 Hz, J3,4 3.2 Hz),
4.05 (br. d, 1H, H-4, J3,4 3.2 Hz, J4,5 < 1 Hz), 4.16–4.24 (m, 4H, H-2,
H-5, H-6a, H-6b), 4.91 (d, 1H, H-1, J1,2 3.7 Hz).
3-Trifluoroacetamidopropyl
2-acetamido-2-deoxy-6-O-sulfo-b-D-
glucopyranoside (triethylammonium salt) 13: 1.30 (t, 9H, NCH2Me,
J 7.3 Hz), 1.87 (m, 2H, CCH2C), 2.06 (s, 3H, NAc), 3.20 (q, 6H, NCH2Me,
J 7.3 Hz), 3.34 and 3.44 (2m, 2×1H, CH2N), 3.52 (dd » br. t, 1H, H-4,
J3,4 9.3 Hz, J4,5 9.5 Hz), 3.58 (dd » br. t, 1H, H-3, J3,4 9.3 Hz, J2,3 9.8 Hz),
3.68 (ddd, 1H, H-5, J4,5 9.5 Hz, J5,6a 5.4 Hz, J5,6b 1.7 Hz), 3.70–3.64 (m,
1H, OCH), 3.73 (dd, 1H, H-2, J1,2 8.6 Hz, J2,3 9.8 Hz), 3.96 (m, 1H, OCH),
4.24 (dd, 1H, H-6a, J5,6a 5.4 Hz), 4.37 (dd, 1H, H-6b, J5,6b 1.7 Hz), 4.54
(d, 1H, H-1, J1,2 8.6 Hz).
3-Aminopropyl 3-O-sulfo-b-D-galactopyranoside (sodium salt) 14:
2.03 (m, 2H, CCH2C), 3.18 (m, 2H, CH2N), 3.68 (dd, 1H, H-2, J1,2
8.1 Hz, J2,3 9.6 Hz), 3.74–3.80 (m, 3H, H-5, H-6a and H-6b), 3.94 and
4.01 (2m, 2×1H, OCH2), 4.29 (br. d, 1H, H-4, J3,4 2.9 Hz, J4,5 < 1 Hz),
4.33 (dd, 1H, H-3, J2,3 9.6 Hz, J3,4 3.9 Hz), 4.54 (d, 1H, H-1, J1,2 8.1 Hz).
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