Compound 9

61-Ethyloxycarbonyl-61-{3-[1-(20-azido-3,6,9,12,15,18-hexaoxatetradecayl)-1H-1,2,3-triazole-4-yl]-propyl-1-oxycarbonyl}-62,62,63,63,64,64,65,65,66,66-deca-{3-[4-(1-α-D-mannopyranosyl-methyl)-1H-1,2,3-triazole-1-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

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InChIKey OFSSRTZMKNSBQC-MFXZVJHLSA-N

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

A 1 M solution of TBAF in THF (0.1 mL, 1 mmol) was added to a mixture of CuSO4.5H2O (3 mg, 19 μmol), sodium ascorbate (12 mg, 60 μmol), 7 (273 mg, 60 μmol) and 8 (481 mg, 1.14 mmol) in THF/H2O (3.5 mL, 0.5:3). The resulting mixture was heated for 1.5 h at 80°C under microwave irradiation. THF and the major part of water were evaporated. Then the crude product was precipitated by addition of a mixture of acetone/CH2Cl2 and extensively washed with CH2Cl2 and acetone. This procedure was repeated three times. A gel permeation chromatography (Sephadex G-50, H2O/MeOH; 90:10) gave 9 as a brown-orange glassy solid (254 mg, 87 %). IR (neat) 3324 (OH), 2107 (N3), 1738 (C=O) cm-1; 1H NMR (400 MHz, D2O), δ: 8.05 (m, 11H; triazole), 4.80(m), 4.43 (m), 3.66 (m), 2.25 (m), 1.24 (m). 13C NMR (100 MHz, D2O), δ: 163.6 (broad), 146.6 (broad), 143.8 (broad), 125.0 (broad), 99.5, 97.8 73.5, 73.0, 71.5, 70.7, 70.2, 70.1, 69.7, 69.3 66.7, 65.6, 64.2, 60.9, 59.8, 50.3, 49.0, 47.2, 39.2, 28.8, 31.8, 28.7, 21.2, 13.6.

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