反应 #302912

反应方程式

3

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

imidazole

TBDPSCl

→

4

收率 85.2%

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

收率 85.2%

溶剂

DMF

反应条件

后处理

1. 1
   其他The mixture was partitioned between EtOAc and sat. aqueous NaHCO3
2. 2
   干燥The organic layer was dried (Na2SO4)
3. 3
   其他evaporated
4. 4
   workup.ADDITIONThe resulting syrupy residue was treated with MeOH (ca. 40 ml)
5. 5
   其他to give the
6. 6
   其他precipitated 4

实验过程

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.

来源