Hydrochloric Acid → 1-(3-O-Benzy-4-hydroxymethyl-beta-D-xylofuranosyl)thymine

Beteiligte Stoffe

Reaktionsschritte

To a stirred solution of nucleoside 4 (9.00 g, 0.014 mol) in methanol (130 cm3) was added sodium methoxide (3.87 g, 0.0716 mol). The reaction mixture was stirred at room temperature for 4 h and then neutralized with dilute hydrochloric acid. The mixture was evaporated to dryness under reduced pressure followed by coevaporation using toulene (15 cm3×3) The residue was purified by silica gel column chromatography using dichloromethane/methanol (4–15% methanol, v/v) as eluent to give nucleoside triol 5 (4.82 g, 89%) as a white solid material after evaporation of the solvents under reduced pressure. δH (CD3OD) 7.89 (1H, d, J 1.2), 7.40–7.24 (5H, m), 5.97 (1H, d, J 6.2), 4.83–4.65 (2H, m), 4.53 (1H, t, J 6.2), 4.21 (1H, d, J 6.2), 3.84 (1H, d, J 12.0), 3.63 (1H, d, J 12.0), 3.59 (2H, d. J 2.6), 1.82 (1H, d, J 1.1). δC (CD3OD) 164.4, 150.9, 137.5, 136.6, 127.5, 127.0, 126.9, 109.8, 86.7, 86.4, 82.8, 78.0, 72.1, 62.3, 61.1, 10.5 (CH3). FAB-MS m/z 379 [M+H]+. Found (%) C, 56.2; H, 6.0; N, 7.0; C18H22N2O7,0.25H2O requires C, 56.5; H, 5.9; N, 7.3.

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