反应 #806268

反应方程式

2-(6-cyano-1-hexyn-1-yl)adenosine

triethyl phosphate

phosphorous oxychloride

sodium hydroxide

→

triethylammonium 2-(6-cyano-1-hexyn-1-yl)adenosine 5′-monophosphate

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   洗涤the resultant mixture was washed with ether
3. 3
   其他The aqueous layer was separated
4. 4
   其他water was removed under reduced pressure
5. 5
   其他the residue was purified by C18 silica gel column chromatography (0.1M triethylammonium acetate buffer:acetonitrile=100:0 to 60:40)
6. 6
   浓缩The thus-obtained fraction was concentrated
7. 7
   其他to thereby remove the triethylammonium acetate buffer
8. 8
   其他The residue was freeze-dried

实验过程

Under argon, A 2-(6-cyano-1-hexyn-1-yl)adenosine (2.41 g) was dissolved in triethyl phosphate (15 mL), and, under ice-cooling conditions, phosphorous oxychloride (25.2 mL, 3.9 eq.) was added thereto, followed by stirring at the same temperature for 5 hours. The reaction mixture was added dropwise to a 10% sodium hydroxide solution (300 mL), and the resultant mixture was washed with ether. The aqueous layer was separated and water was removed under reduced pressure, and the residue was purified by C18 silica gel column chromatography (0.1M triethylammonium acetate buffer:acetonitrile=100:0 to 60:40). The thus-obtained fraction was concentrated, and the concentrate was subjected to C18 silica gel column chromatography (water:acetonitrile=100:0 to 60:40), to thereby remove the triethylammonium acetate buffer. The residue was freeze-dried, to thereby yield 1.14 g of the above-titled compound as a colorless amorphous substance.

来源