Hydrochloric Acid → 5'-o-Tert-butyldimethylsilyl-5-iodouridine

Participants

Reaction Steps

Imidazole (216 mg) was added to a mixture of triol 3a (490 mg) and tert-butyldimethylchlorosilane (239 mg) in 1 mL of DMF cooled by an ice bath. The mixture was allowed to warm to room temperature. After 16 hours, the mixture was poured into 0.1 M HCl (25 mL) and extracted with ethyl acetate (3×50 mL), the aqueous phases were washed with water, dried over anhydrous MgSO4, and concentrated in vacuo. Purification by flash chromatography (7% MeOH/CH2Cl2) gave 460 mg of the product as a colorless solid: 1H NMR (DMSO-d6) δ 0.08-0.12 (m, 6), 0.90 (s, 9), 3.72 (dd, 1), 3.80 (dd, 1), 3.90 (bs, 2), 4.02-3.98 (m, 1), 5.76 (d, 1), 7.93 (s, 1), 11.74 (bs, 1).

Provenance & Evidence