反应 #1435754

反应方程式

uridine

diphenyl carbonate

hexamethylphosphoric triamide

→

title compound 15

收率 84.0%

1-(β-D-Arabinofuranosyl)uracil

收率 84.0%

溶剂

water

反应条件

后处理

1. 1
   温度was heated
2. 2
   温度cooled to room temperature
3. 3
   洗涤washed with CHCl3
4. 4
   workup.ADDITIONEt3N (25 mL) was added
5. 5
   温度the aqueous solution was heated at 70° C. for 5 h
6. 6
   其他The solvent was evaporated in vacuo
7. 7
   其他the residue was crystallized from MeOH/water

实验过程

A mixture of uridine (14; 13.25 g, 54.5 mmol), diphenyl carbonate (15.48 g, 72.5 mmol), anhydrous NaHCO3 (349 mg, 4.15 mmol), and hexamethylphosphoric triamide (50 mL) was heated with stirring at 150° C. under nitrogen for 20 min, and then cooled to room temperature. The mixture was poured into cold water (400 mL), and washed with CHCl3. Et3N (25 mL) was added, and the aqueous solution was heated at 70° C. for 5 h. The solvent was evaporated in vacuo, and the residue was crystallized from MeOH/water to give the title compound 15 as a white solid (11.13 g, 84%). 1H NMR (DMSO-d6) δ 11.2 (s, 1H, NH), 7.60 (d, J=7.5 Hz, 1H, H-6), 5.95 (d, 1H, H-1′), 5.51 (d, J=7.5 Hz, 1H, H-5), 6.30–5.30 (br, 2H, 2 OH), 4.10–3.50 (m, 6H, H-2′, H-3′, H-4′, H-5′, OH).

来源