반응 #1994282

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( 34 )

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

TBAF

→

Product ( 35 )

수율 75.4%

3′-O-Allyl-5-iodo-2′-deoxyuridine

수율 75.4%

용매

THF

반응 조건

후처리

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

실험 절차

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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