Preparation of 6-azafulleroid-6-deoxy-2,3-di- O-myristoylcellulose

[Display omitted] ► We prepared fullerene (C 60)-containing cellulose derivative with degree of substitution of C 60 of 0.33. ► It was characterized by FT-IR, 13C NMR, UV–vis, DPV, SEC analyses. ► Microwave heating was effective for shortening reaction time. 6-Azafulleroid-6-deoxy-2,3-di- O-myristoy...

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Veröffentlicht in:Carbohydrate research 2011-11, Vol.346 (15), p.2515-2518
Hauptverfasser: Ichihara, Nobuhiko, Takano, Toshiyuki, Sakakibara, Keita, Kamitakahara, Hiroshi, Nakatsubo, Fumiaki
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Sprache:eng
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Zusammenfassung:[Display omitted] ► We prepared fullerene (C 60)-containing cellulose derivative with degree of substitution of C 60 of 0.33. ► It was characterized by FT-IR, 13C NMR, UV–vis, DPV, SEC analyses. ► Microwave heating was effective for shortening reaction time. 6-Azafulleroid-6-deoxy-2,3-di- O-myristoylcellulose ( 3) was synthesized from 6-azido-6-deoxycellulose ( 1) by two reaction steps. The myristoylation of compound 1 with myristoyl chloride/pyridine proceeded smoothly to give 6-azido-6-deoxy-2,3-di- O-myristoylcellulose ( 2) in 97.0% yield. The reaction of compound 2 with fullerene (C 60) was carried out by microwave heating to afford compound 3 in high yield. It was found from FT-IR, 13C NMR, UV–vis, differential pulse voltammetry (DPV), SEC analyses that compound 3 was the expected C 60-containing polymer. Consequently, maximum degree of substitution of C 60 (DS C60) of compound 3 was 0.33.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2011.08.013