反应详情

To a suspension of 5-iodo-2'deoxycytidine (17.65g, 50.00 mmol) in 250 ml of dry pyridine at 0° (ice bath) is added p-toluenesulfonyl chloride (11.50g, 60.00 mmol). The reaction mixture is stirred at 0° for 1 h and then stored at 3° in the dark with stirring for an additional 23 h. At the end of the reaction a clear solution is obtained, to which 15 ml of methanol is added. After standing for 30 min, the solvent is removed under diminished pressure at room temperature to afford a syrup which is coevaporated several times with methanol. The residue is triturated with icecooled water to give a crystalline mass which is broken down to the fine particles with a spatula. The solid material is collected by filtration, washed thoroughly with water, a small amount of ice-cooled ethanol, ether, and dried in vacuo to yield 20.24 g (80%) of the desired product.

1. customstored at 3° in the dark
2. stirringwith stirring for an additional 23 h
3. customAt the end of the reaction a clear solution
4. additionis added
5. waitAfter standing for 30 min
6. customthe solvent is removed under diminished pressure at room temperature
7. customto afford a syrup which
8. customThe residue is triturated with icecooled water
9. customto give a crystalline mass which
10. filtrationThe solid material is collected by filtration
11. washwashed thoroughly with water
12. temperaturea small amount of ice-cooled ethanol, ether
13. customdried in vacuo