[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].C1(C)C=CC=CC=1.[C:25](Cl)(=[O:29])[C:26]([CH3:28])=[O:27].CO.C(Cl)Cl>CN(C=O)C.N1C=CC=CC=1>[C:25]([O:8][CH2:7][C@H:6]1[O:9][C@@H:1]([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@H:2]([OH:3])[C@@H:4]1[OH:5])(=[O:29])[C:26]([CH3:28])=[O:27]Uridine (3.0 g, 12 mmol) was dried by toluene azeotrope under vacuum (3×), and then dissolved in DMF (20 mL) and pyridine (20 mL). The resultant solution was cooled to −10 degrees C. and 6.0 mL of pyruvyl chloride (produced in step A above) was added dropwise. The reaction mixture was stirred at room temperature under argon for 24 hours. Analysis by TLC (5% MeOH/CH2Cl2) showed the consumption of uridine. The reaction mixture was evaporated to dryness and partitioned between CH2Cl2 and aqueous sodium bicarbonate. The organic layer was washed with water, aqueous HCl (pH 3.0), and water; dried over sodium sulfate; concentrated; and purified using flash chromatography (silica gel, 5% MeOH/C2Cl2) to yield 1.4 g of uridine pyruvate, or 2′,3′,5′-tri-O-pyruvyluridine.
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