반응 #1994281

반응 방정식

TBDMSCl

5-iodo-2′-deoxyuridine

imidazole

→

product ( 33 )

수율 90.0%

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

수율 90.0%

용매

N,N-dimethylformamide

반응 조건

후처리

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

실험 절차

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.

출처