Compound 15a

61-Ethyloxycarbonyl-61-(6-azidohexyl-1-oxycarbonyl)-62,62,63,63,64,64,65,65,66,66-deca-{3-[1-(2-α-D-mannopyranosyl-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-ROOCQCEXSA-N

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

A mixture of compound 14a (140 mg, 0.03 mmol) and sodium azide (8 mg, 0.120 mmol) in DMSO (2 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 15a (117 mg, 84%) as a red solid. FTIR (KBr): 3385 (OH), 2099 (N3), 1740 (C=O) cm-1; 1H NMR (700 MHz, DMSO-d6), δ: 7.85 (s, 10H), 4.68 (m, 12H), , 4.59 – 4.09 (m, 44H), 3.91 (s, 8H), 3.76 (s, 8H), 3.61 (m, 8H), 3.53 (s, 8H), 3.46 – 3.25 (m, 96H), 3.12 (m, 4H), 2.04 (m, 24H), 1.36 – 0.98 (m, 32H); 13C NMR (175 MHz, , DMSO-d6), δ: 163.3, 146.1, 145.8, 141.4, 122.7, 100.2, 78.6, 74.5, 71.2, 70.5, 67.2, 65.3, 61.6, 52.5, 52.0, 49.6, 28.2, 21.8, 14.4; MS (MALDI-TOF) calculated for [M]+ C216H237N33O84= 4636,53; found: 4659 [M+Na]+.

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