Compound 5

61-Ethyloxycarbonyl-61-[5-(trimethylsilyl)pent-4-yn-1-oxycarbonyl]-62,62,63,63,64,64,65,65,66,66-deca(3-azidopropyloxycarbonyl)-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 ADKGXBMSJGRGES-UHFFFAOYSA-N

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

DBU (0.5 ml, 3 mmol) was added to a stirred solution of 3 (140 mg, 0.14 mmol), CBr4(4.7 g, 14 mmol) and 4 (459 mg, 1.7 mmol) in ODCB (30 mL) at room temperature. The resulting solution was stirred for 72 h, then filtered through a short plug of SiO2 (CH2Cl2) and evaporated. Column chromatography (SiO2, cyclohexane/AcOEt, 2:1) gave 5 (220 mg, 67%). Caution: owing to its high number of azide residues, this compound must be handled with special care. Upon evaporation, compound 5 has never been dried under high vacuum and the use of metallic spatula avoided. Furthermore, this compound has been always prepared on a small scale. Orange glassy product. IR (neat): 2176 (C≡C), 2092 (N3), 1739 (C=O).1H NMR (CDCl3, 300 MHz), δ: 4.35 (m, 24H), 3.41 (m, 20H), 2.34 (t, J = 7 Hz, 2H), 1.95 (m, 22H), 1.34 (t, J = 7.0 Hz, 3H), 0.15 (s, 9H).13C NMR (CDCl3, 75 MHz), δ: 163.4, 145.7, 141.2, 105.185.7, 69.0, 65.5, 63.8, 63.1, 47.8, 45.3, 27.9, 27.4, 16.4, 14.0, 0.0.

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