反应 #543570

反应方程式

Acetone

Hydrazine hydrate

1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)uracil

→

2

收率 68.0%

1-(3,5-Di-O-benzoyl-β-L-xylofuranosyl)uracil

收率 68.0%

溶剂

acetic acid

pyridine

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred for 30 minutes
2. 2
   其他The reaction mixture was evaporated under reduced pressure
3. 3
   其他The resulting residue was purified by silica gel column chromatography [eluent

实验过程

Hydrazine hydrate (1.4 mL, 28.7 mmol) was added to a solution of 1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)uracil 1 [Ref.: Gosselin, G.; Bergogne, M.-C.; Imbach, J.-L., “Synthesis and Antiviral Evaluation of β-L-Xylofuranosyl Nucleosides of the Five Naturally Occurring Nucleic Acid Bases”, Journal of Heterocyclic Chemistry, October–November 1993, 30, 1229–1233] (4.79 g, 9.68 mmol) in pyridine (60 mL) and acetic acid (15 mL). The solution was stirred overnight at room temperature. Acetone was added (35 mL) and the mixture was stirred for 30 minutes. The reaction mixture was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography [eluent: stepwise gradient of methanol (0–4%) in dichloromethane to give 2 (3.0 g, 68%) which was crystallized from cyclohexane/dichloromethane: mp=111–114° C.; 1H-NMR (DMSO-d6): δ 11.35 (br s, 1H, NH), 7.9–7.4 (m, 11H, 2 C6H5CO, H-6), 6.38 (d, 1H, OH-2′, JOH-2′=4.2 Hz), 5.77 (d, 1H, H-1′, J1′-2′=1.9 Hz), 5.55 (d, 1H, H-5, J5-6=8 Hz), 5.54 (dd, 1H, H-3′, J3′-2′=3.9 Hz and J3′-4′=1.8 Hz), 4.8 (m, 1H, H-4′), 4.7 (m, 2H, H-5′ and H-5″), 4.3 (m, 1H, H-2′); MS: FAB>0 (matrix GT) m/z 453 (M+H)+, 105 (C6H5CO)+; FAB<0 (matrix GT) m/z 451 (M−H)−, 121 (C6H5CO2)−, 111 (B)−; Anal. Calcd for C23H20N2O8.H2O: C, 58.09; H, 4.76; N, 5.96. Found: C, 57.71; H, 4.42; N, 5.70.

来源