Reacción #1994282

Ecuación de reacción

( 34 )

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

TBAF

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Product ( 35 )

Rendimiento 75.4%

3′-O-Allyl-5-iodo-2′-deoxyuridine

Rendimiento 75.4%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente