Compound 17c

61,61,62,62,63,63,64,64,65,65,66,66-Dodeca-3-{{1-{61-Ethyloxycarbonyl-62,62,63,63,64,64,65,65,66,66-deca-{[1-(1-α-D-mannopyranosyl-methyl)-1H-1,2,3-triazole-4-yl]-propyl-1-oxycarbonyl}-1,9:16,17:21,40:30,31:44,45:52,60-hexa(methano)[60]fullerene-61-yl}-20-(3-carbonyloxypropyl-1H-1,2,3-triazole-4-yl)-3,6,9,12,15,18-hexaoxatetradecayl)}-1H-1,2,3-triazole-4-yl}-propyl-1-oxycarbonyl-1,9:16,17:21,40:30,31:44,45:52,60-hexa(methano)[60]fullerene

From: Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection

| 1H NMR | 13C NMR | DEPT 135 | IR | ChemDraw

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

A mixture of 9 (254 mg, 52 μmol), 16 (10.1 mg, 3 μmol), CuSO4.5H2O (1 mg, 6 μmol) and sodium ascorbate (3 mg, 15 μmol) in THF/H2O (3.5 mL, 0.5:3) was heated at 80°C under microwave irradiation in a sealed tube. After 2 hours, the mixture was evaporated. Exclusion column chromatography (Econo-Pac® 10 DG, BIO-RAD, H2O) followed by a dialysis against milli-Q water (Molecular Weigth CutOff: 25000) gave 17c (155 mg, 76 %). Brown-orange glassy solid. IR (neat) 3251 (OH), 1732 (C=O) cm-1; 1H NMR (400 MHz, DMSO-d6), δ: 8.10 (s, 120H), 7.83 (s, 24H), 4.90-3.18 (m, 1272H), 3.85-3.28 (m, 744H), 2.74-2.63 (m, 48H), 2.38-2.11 (m, 240H), 2.08-1.91 (m, 48H), 1.25-1.11 (m, 36H). 13C NMR (100 MHz, DMSO-D6), δ: 162.9, 145.5, 143.7, 140.6, 124.0, 122.3, 99.0, 74.1, 70.9, 70.2, 69.8, 69.7 (two peaks), 69.6, 69.2, 68.7, 67.0, 64.2, 61.3, 59.1, 50.0, 49.2, 46.1, 44.2, 28.6, 27.7, 21.3, 13.7.

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