反応 #82914

反応方程式

3'-O-(t-butyldiphenylsilyl)-5'-deoxy-5'-iododthymidine

3'-O-(t-Butyldiphenylsilyl)-5'-Deoxy-5'-Iodothymidine

AIBN

→

title compound

3'-O-(t-Butyldiphenylsilyl)-5'-Deoxy-5'-C-Allylthymidine

溶媒

toluene

反応条件

後処理

1. 1
   温度The solution was cooled
2. 2
   濃縮concentrated under vacuo
3. 3
   その他The residue was purified by silica gel column chromatography and on elution with hexanes:EtOAc (1:1

実験手順

A stirred solution of 3'-O-(t-butyldiphenylsilyl)-5'-deoxy-5'-iododthymidine (12, 1.77 g, 3 mmol), allytributyltin (2.97 g, 9 mmol) and AIBN (0.54 g, 3.3 mmol) in dry toluene (30 ml) was degassed completely and heated at 65° C. for 6 hr. The solution was cooled and concentrated under vacuo. The residue was purified by silica gel column chromatography and on elution with hexanes:EtOAc (1:1, v/v) furnished the title compound as homogeneous material. Appropriate fractions were pooled and evaporated to furnish 46, 0.75 g of a white foam, 50% yield. The structure was confirmed by 1H NMR.

出典