Thymidine → 1-(2-Deoxy-5-O-(triphenylmethyl)pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
Reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@@H:21]1([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[CH2:22]1>N1C=CC=CC=1>[C:1]([O:27][CH2:26][C@H:25]1[O:28][C@@H:21]([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[CH2:22][C@@H:23]1[OH:24])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
In a 250-ml three-necked flask, trityl chloride is placed in anhydrous pyridine under inert gas and stirring, and the thymidine is added. After 30 minutes of heating to t=110° C. (heating-bath temperature), the yellowish reaction solution is allowed to cool and is then decanted slowly into 1.5 l of vigorously stirred ice water. After 30 minutes of stirring, the milky-white suspension is suction-filtered, the filter cake is dissolved in acetone and the solution is filtered once again. The solvent is removed in the rotary evaporator and the solid is dried for 16 hours in high vacuum. The product, 5′-O-tritylthymidine, is obtained by recrystallization two times from a benzene-acetone mixture.