تفاعل #1994282

معادلة التفاعل

( 34 )

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

TBAF

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Product ( 35 )

المردود 75.4%

3′-O-Allyl-5-iodo-2′-deoxyuridine

المردود 75.4%

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر