تفاعل #1994281

معادلة التفاعل

TBDMSCl

5-iodo-2′-deoxyuridine

imidazole

→

product ( 33 )

المردود 90.0%

5′-O-(t-Butyldimethylsilyl)-5-iodo-2′-deoxyuridine

المردود 90.0%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched with sat. aq. NaCl solution
2. 2
   استخلاصextracted with EtOAc
3. 3
   تجفيفAfter drying (MgSO4)
4. 4
   أخرىthe solvent was removed
5. 5
   أخرىthe crude mixture was purified by chromatography on silica (EtOAc:petroleum ether 3:7)

الإجراء التجريبي

To a solution of 5-iodo-2′-deoxyuridine (5.0 g, 14 mmol) in 70 ml in dry N,N-dimethylformamide (DMF) was added imidazole (1.09 g, 16 mmol), followed by (2.41 g, 16 mmol) TBDMSCl at 0° C. The mixture was left in the ice bath and stirred overnight. The reaction was quenched with sat. aq. NaCl solution and extracted with EtOAc. After drying (MgSO4), the solvent was removed and the crude mixture was purified by chromatography on silica (EtOAc:petroleum ether 3:7). The product (33) (5.9 g, 90%) was obtained as a colourless solid. 1H NMR (d6 DMSO) δ 0.00 (s, 3H, CH3), 0.79 (s, 9H, tBu), 1.88-1.97 (m, 1H, H-2′), 2.00-2.05 (m, 1H, H-2′), 3.59-3.71 (m, 2H, H-5′), 3.75 (br s, 1H, H-4′), 4.06 (br s, 1H, H-3′), 5.18 (d, J=4.0 Hz, 1H, OH), 5.98 (t, J=5.9 Hz, 1H, H-1′), 7.89 (s, 1H, H-6), 11.62 (s, 1H, NH). Mass (−ve electrospray) calcd for C15H25IN2O5Si 468.06. Found 467.

المصدر