Compound 15b

61-Ethyloxycarbonyl-61-(6-azidohexyl-1-oxycarbonyl)-62,62,63,63,64,64,65,65,66,66-deca-{3-[1-(2-β-D-galactopyranosyl-ethyl)-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

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InChIKey CFKRLTPEUXLFSU-GWBXZXKQSA-N

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

A mixture of compound 14b (30 mg, 0.007 mmol) and sodium azide (5 mg, 0.077 mmol) in DMSO (1.5 mL) was deoxygenated with argon for 5 min and heated 3 h under microwave irradiation (70°C). AcOEt was added and the precipitate was centrifuged, washed with MeOH and MeOH/AcOEt 3:1, then dried under high vacuum to give compound 15b (26 mg, 81%) as a red solid. FTIR (KBr): 3123 (OH), 2097 (N3), 1740 (C=O) cm-1; 1H NMR (700 MHz, DMSO-d6), δ: 7.83 (s, 10H), 4.84– 4.72(m, 12H), , 4.64 – 4.16 (m, 44H), 3.94 (s, 8H), 3.74 (s, 8H), 3.63–3.52 (m, 16H), 3.41–3.18 (m, 96H), 2.10 (s, 24H), 1.40–0.95 (m, 32H); 13C NMR (175 MHz, DMSO-d6), δ: 163.4, 146.1, 145.5, 141.2, 123.1, 100.2, 78.2, 77.9, 74.5, 71.3, 70.5, 67.2, 65.1, 61.4, 52.4, 49.4, 28.3, 25.4, 21.9, 14.2; MS (MALDI-TOF) calculated for [M]+ C216H237N33O84= 4636,53; found: 4638.

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