Réaction #1994282

Équation de réaction

( 34 )

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

TBAF

→

Product ( 35 )

Rendement 75.4%

3′-O-Allyl-5-iodo-2′-deoxyuridine

Rendement 75.4%

Solvants

THF

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source