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H-6a, H-5, H-6a0, H-6b0), 3.57–3.50 (3H, m, H-6b, H-2,
H-30), 3.46–3.42 (2H, m, H-4, H-40), 3.32 (3H, s, OCH3);
13C NMR (300 MHz, CDCl3): d 138.43, 138.39, 138.24,
128.68, 128.63, 128.26, 127.91, 127.72, 100.38, 98.11,
82.25, 80.65, 77.45, 77.39, 77.02, 76.96, 75.04, 74.34,
73.55, 73.25, 70.94, 68.57, 60.61, 55.38; HRMS: calcd
for C34H42O11Na [M+Na]+ 649.2629, found m/z
649.2625.
H-10), 4.22 (1H, dd, J1 3.5 Hz, J2 8 Hz, H-50), 4.09–4.04
(2H, m, H-6a, H-20), 3.97–3.90 (3H, m, H-6b, H-5, H-
30), 3.88–3.76 (3H, m, H-4, H-2, H-40), 3.74–3.67 (2H,
m, H-3, H-6b0) 3.65–3.61 (1H, m, H-6a0); b-anomer,
5.02 (1H, d, J 1.5 Hz, H-10), 4.56 (1H, d, J 7.75 Hz,
H-1), 4.22 (1H, dd, J1 3.5, J2 8 Hz, H-50), 4.09–4.04
(2H, m, H-6a, H-20), 3.97–3.90 (2H, m, H-5, H-30),
3.88–3.76 (3H, m, H-6b, H-4, H-40), 3.74–3.67 (1H, m,
H-6b0), 3.65–3.61 (2H, m, H-6a0, H-3), 3.47 (1H, dd,
J1 7.75 Hz, J2 10 Hz, H-2); 13C NMR (300 MHz,
D2O): d 107.95, 96.63, 92.51, 83.05, 81.19, 76.88,
73.88, 72.89, 71.99, 70.99, 69.08, 67.6, 62.87; LRMS:
calcd for C12H22O11Na [M+Na]+ 365.0, found m/z
365.0.
1.8. Methyl 2,3,4-tri-O-allyl-6-O-(2-acetamido-2-deoxy-
a-D-galactopyranosyl)-a-D-glucopyranoside (9)
Disaccharide 9 was obtained by the same protocol as de-
1
scribed for 6. H NMR (500 MHz, CDCl3): d 5.99–5.90
(3H, m, 3CHAll), 5.34–5.19 (6H, m, 3 · CH2 All), 4.84
(1H, d, J 3.5 Hz, H-10), 4.77 (1H, d, J 3.5, H-1), 4.36–
4.12 (6H, m, 3 · CH2 All), 3.92–3.76 (6H, m, H-6a, H-
6b, H-3, H-6b0, H-50, H-30), 3.67–3.56 (3H, m, H-5, H-
6a0, H-40), 3.51 (1H, m, H-2), 3.43 (3H, s, OCH3),
3.37–3.30 (2H, m, H-4, H-20), 1.68 (3H, s, CH3CO);
13C NMR (300 MHz, CDCl3): d 171.27, 135.13,
134.70, 133.31, 117.64, 117.07, 116.56, 106.62, 98.14,
86.69, 81.29, 79.45, 77.52, 77.25, 74.21, 73.79, 72.58,
70.55, 69.59, 65.41, 64.36, 61.42, 55.20, 52.12, 23.05;
LRMS: calcd for C24H39NO11Na [M+Na]+ 540.2,
found m/z 540.2.
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