Réaction #302912

Équation de réaction

3

1-[5-O-Benzoyl-3-O-(t-butyldimethylsilyl)-2-deoxy-4-(trimethylsilyl)ethynyl-β-D-threo-pentofuranosyl]thymine

imidazole

TBDPSCl

→

4

Rendement 85.2%

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

Rendement 85.2%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe mixture was partitioned between EtOAc and sat. aqueous NaHCO3
2. 2
   SéchageThe organic layer was dried (Na2SO4)
3. 3
   Autreevaporated
4. 4
   workup.ADDITIONThe resulting syrupy residue was treated with MeOH (ca. 40 ml)
5. 5
   Autreto give the
6. 6
   Autreprecipitated 4

Mode opératoire

A mixture of 3 (10.35 g, 60.1 mmol), imidazole (8.18 g, 120.2 mmol), and TBDPSCl (15.6 ml, 60.1 mmol) in DMF (40 ml) was stirred for 16 h at room temperature under positive pressure of dry Ar. The mixture was partitioned between EtOAc and sat. aqueous NaHCO3. The organic layer was dried (Na2SO4) and evaporated. The resulting syrupy residue was treated with MeOH (ca. 40 ml) to give the precipitated 4. This procedure was repeated further 3 times to give 4 (18.97 g, 77%) as a white solid.

Source