反应 #302913

反应方程式

O2

4

1-[5-O-Benzoyl-2-deoxy-4-ethynyl-β-D-threo-pentofuranosyl]thymine

Et3N

Me3SiOSO2CF3

→

5

收率 88.0%

1-[5-O-Benzoyl-2-deoxy-4-ethynyl-3-O-methanesulfonyl-β-D-threo-pentofuranosyl]thymine

收率 88.0%

反应条件

后处理

1. 1
   其他partitioned between CH2Cl2 and sat. aqueous NaHCO3
2. 2
   干燥The organic layer was dried (Na2SO4)
3. 3
   其他evaporated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in DMSO (12 mL)
5. 5
   其他The mixture was partitioned between EtOAc and brine
6. 6
   干燥The organic layer was dried (Na2SO4)
7. 7
   其他evaporated
8. 8
   其他chromatographed on a silica gel column (hexane/EtOAc=5/1)

实验过程

To a stirring mixture of 4 (3.58 g, 8.72 mmol) and Et3N (6.1 ml, 43.6 mmol) was added Me3SiOSO2CF3 (2.56 mL, 13.0 mmol) at 0° C. under positive pressure of dry Ar. The mixture was stirred for 30 min at the same temperature, and then partitioned between CH2Cl2 and sat. aqueous NaHCO3. The organic layer was dried (Na2SO4) and evaporated. The residue was dissolved in DMSO (12 mL). To this solution was added Pd(OAc)2 (98 mg, 0.44 mmol), and the mixture was stirred for 36 h under positive pressure of O2. The mixture was partitioned between EtOAc and brine. The organic layer was dried (Na2SO4), evaporated, and chromatographed on a silica gel column (hexane/EtOAc=5/1) to give 5 (3.13 g, 88%) as a white solid.

来源