反応 #1994282

反応方程式

( 34 )

3′-O-Allyl-5′-O-t-butyldimethylsilyl-5-iodo-2′-deoxyuridine

TBAF

→

Product ( 35 )

収率 75.4%

3′-O-Allyl-5-iodo-2′-deoxyuridine

収率 75.4%

溶媒

THF

反応条件

後処理

1. 1
   その他The reaction was quenched
2. 2
   workup.ADDITIONby adding sat. NaCl solution (20 ml)
3. 3
   抽出extracted with EtOAc three times
4. 4
   乾燥The combined organic layers were dried over MgSO4
5. 5
   その他The crude mixture was purified by chromatography on silica (EtOAc:petrol 7:3)

実験手順

To a solution of (34) (2.34 g, 4.71 mmol) in dry THF (40 ml) was added at 0° C. TBAF (5.2 ml, 5.2 mmol, 1 M solution in THF). The reaction mixture was allowed to warm up to room temperature and was then stirred for 16 h. The reaction was quenched by adding sat. NaCl solution (20 ml) and extracted with EtOAc three times. The combined organic layers were dried over MgSO4. The crude mixture was purified by chromatography on silica (EtOAc:petrol 7:3). Product (35) (1.4 g, 75%) was isolated as a colourless solid. 1H NMR (d6 DMSO) δ 2.02-2.39 (m, 2H, H-2′), 3.42-3.52 (m, 2H, H-5′), 3.84-3.88 (m, 3H, H-4′, CH2], 3.97-4.00 (m, 1H, H-3′), 5.02-5.09 (m, 2H, OH, ═CH2), (dd, J=1.9, 17.3 Hz, 1H, ═CH2), 5.73-5.82 (m, 1H, CH═), 5.94 (t, J=6.8 Hz, 1H, H-1′), 8.24 (s, 1H, H-6), 11.56 (s, 1H, NH). Mass (−ve electrospray) calcd for C12H16IN2O5 394.0. Found 393.

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