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Volumn 8, Issue 6, 2008, Pages 3136-3141

Sonochemical reaction of fullerene[C 60] with several 2′-azidoethyl per-O-acetyl glycosides

Author keywords

2 azidoethyl per O acetyl glycosides; Cycloadditive reaction; Fullerene C 60 ; Ultrasonication

Indexed keywords

CYCLOADDITIVE REACTION; FULLERENE C; FULLERENE[C 60]; SONOCHEMICAL; ULTRASONICATION;

NANOSTRUCTURES;

FULLERENES;

EID: 48449087237 PISSN: 15334880 EISSN: None Source Type: Journal
DOI: 10.1166/jnn.2008.091 Document Type: Article

Times cited : (8)

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- 2′-azidoethyl glycosides synthesis-A solution of 2′-chloroethyl glycoside (1.46 g, 3.55 mmol) and sodium azide (443 mg, 7.10 mmol) in DMF (70 mL) was stirred for 4 h at 110 °C. The reaction mixture was cooled to room temperature and then the solvent removed in vacuo. The residual syrup was diluted with CH2Cl2, washed with water, dried, and concentrated to a syrup. The crude product was purified by silica gel column chromatography (toluene/EtOAc, 5/1 v/v) to give 2′-azidoethyl glycosides la-le, respectively. 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (la, Rf 0.29 (Tol/EtOAc 5/3 v/v, 90% yield; m.p. 78.6-79.6 °C (EtOAc-Hex, lit.13 m.p. 75-77 °C, 1H-NMR (400 MHz, CDC13) δ 5.33-5.23 (m, 3 H, 4.83 (d, 1 H, J1.2, 2.0 Hz, H-1, 4.25 (dd, 1 H, J, 5.2, 12.4 Hz, H-6a, 4.08 (dd, 1 H. J, 2.8, 12.2 Hz, H-6b, 4.03-3.99 m, 1 H, H-5, 3.86-3.81 and 3.66-3.60
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