反应详情

11.7 g. of Isopropylidene adenosine were dissolved in 3.5 liters of water and the pH was adjusted to 12.2 by the addition of 5.85 g. of potassium hydroxide. 23.7 g. of potassium permanganate in 825 ml. of water were added dropwise with stirring over a period of 33/4 hours. The solution was then allowed to sit at room temperature overnight. The excess permanganate was destroyed by the dropwise addition of 30% hydrogen peroxide and the reaction mixture was filtered through a layer of NH3 -washed celite. The yellow filtrate was concentrated in vacuo at 35°-45° to 600 ml. and the acid precipitated in an ice bath by adjusting the pH to 4.5 by the dropwise addition of 1:3 HCl. The white precipitate was washed with dilute (1:1000) acetic acid and dried at 135°C. to yield 7.93 g. of the crude isopropylidene product, m.p. 265-8°. The material was taken up in 100 ml. of dilute NH3, and recrystallized by adjusting the pH to 4.5 by the addition of 1:3 acetic acid to yield 7.7 g. of 2',3'-isopropylidene adenosine-5'-carboxylic acid, m.p. 272-3°.

1. additionthe pH was adjusted to 12.2 by the addition of 5.85 g
2. customThe excess permanganate was destroyed by the dropwise addition of 30% hydrogen peroxide
3. filtrationthe reaction mixture was filtered through a layer of NH3 -washed celite
4. concentrationThe yellow filtrate was concentrated in vacuo at 35°-45° to 600 ml
5. customand the acid precipitated in an ice bath
6. additionby the dropwise addition of 1:3 HCl
7. washThe white precipitate was washed
8. additionwith dilute (1:1000) acetic acid
9. customdried at 135°C.
10. customto yield 7.93 g
11. customof dilute NH3, and recrystallized
12. additionby the addition of 1:3 acetic acid
13. customto yield 7.7 g