Réaction #302913

Équation de réaction

O2

4

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

Et3N

Me3SiOSO2CF3

→

5

Rendement 88.0%

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

Rendement 88.0%

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source