反応 #1994281

反応方程式

TBDMSCl

5-iodo-2′-deoxyuridine

imidazole

→

product ( 33 )

収率 90.0%

5′-O-(t-Butyldimethylsilyl)-5-iodo-2′-deoxyuridine

収率 90.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   その他The reaction was quenched with sat. aq. NaCl solution
2. 2
   抽出extracted with EtOAc
3. 3
   乾燥After drying (MgSO4)
4. 4
   その他the solvent was removed
5. 5
   その他the crude mixture was purified by chromatography on silica (EtOAc:petroleum ether 3:7)

実験手順

To a solution of 5-iodo-2′-deoxyuridine (5.0 g, 14 mmol) in 70 ml in dry N,N-dimethylformamide (DMF) was added imidazole (1.09 g, 16 mmol), followed by (2.41 g, 16 mmol) TBDMSCl at 0° C. The mixture was left in the ice bath and stirred overnight. The reaction was quenched with sat. aq. NaCl solution and extracted with EtOAc. After drying (MgSO4), the solvent was removed and the crude mixture was purified by chromatography on silica (EtOAc:petroleum ether 3:7). The product (33) (5.9 g, 90%) was obtained as a colourless solid. 1H NMR (d6 DMSO) δ 0.00 (s, 3H, CH3), 0.79 (s, 9H, tBu), 1.88-1.97 (m, 1H, H-2′), 2.00-2.05 (m, 1H, H-2′), 3.59-3.71 (m, 2H, H-5′), 3.75 (br s, 1H, H-4′), 4.06 (br s, 1H, H-3′), 5.18 (d, J=4.0 Hz, 1H, OH), 5.98 (t, J=5.9 Hz, 1H, H-1′), 7.89 (s, 1H, H-6), 11.62 (s, 1H, NH). Mass (−ve electrospray) calcd for C15H25IN2O5Si 468.06. Found 467.

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