Compound 14b

61-Ethyloxycarbonyl-61-(6-bromohexyl-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 DEJXLWMBIAFBLC-GWBXZXKQSA-N

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

A mixture of 12 (35 mg, 0.016 mmol), 13b (72 mg, 0.29 mmol), CuBr∙S(CH3)2 (16 mg, 0.08 mmol), sodium ascorbate (25 mg, 0.12 mmol) and a piece of copper metal wire in DMSO (2 mL) was deoxygenated and kept under argon with vigorous stirring for 48 h. The crude reaction was filtered through a QuadraSilTM Mercaptopropyl column. Et2O was added to the mixture and the precipitate was centrifuged and extensively washed with AcOEt, then dried under high vacuum to give compound 14b (64 mg, 86 %) as a dark red solid. FTIR (KBr): 3422 (OH), 1740 (C=O) cm-1; 1H NMR (700 MHz, DMSO-d6), δ: 7.93 (s, 10H), 5.01–4.72 (m, 12H), , 4.64–4.18 (m, 44H), 3.86 (s, 8H), 3.78 (s, 8H), 3.61–3.53 (m, 16H), 3.41–3.18 (m, 96H), 3.09 (m, 4H), 2.10 (s, 24H), 1.40–0.95 (m, 32H); 13C NMR (175 MHz, DMSO-d6), δ: 177.1, 167.8, 163.1, 147, 146.1, 145, 140.8, 124.7, 123.2, 103.9, 97.8, 82.7, 75.7, 73.9, 70.8, 69.1, 68.8, 68.5, 67.3, 63.5, 61, 60.2, 49.9, 28.1, 21.9, 15.5; MS (MALDI-TOF) calculated for [M]+ C216H237BrN30O84= 4673.44; found: 4674.

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