Réaction #1994284

Équation de réaction

tert-butyldimethylsilyl chloride

5-iodo-2′-deoxycytidine

imidazole

→

expected product ( 39 )

Rendement 72.1%

5′-O-(tert-Butyldimethylsilyl)-5-iodo-2′-deoxycytidine

Rendement 72.1%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Autrethe volatiles were evaporated under reduced pressure
2. 2
   Autrethe residue purified by flash chromatography on silica gel with EtOAc:MeOH (95:5 to 90:10)

Mode opératoire

To a solution of 5-iodo-2′-deoxycytidine (2.2 g, 6.23 mmol) in DMF (130 ml) was added imidazole (467 mg, 6.85 mmol). The mixture was cooled at 0° C. and tert-butyldimethylsilyl chloride (TBDMSCl) (1.33 g, 6.85 mmol) added over 5 minutes. After 18 h at room temperature, the volatiles were evaporated under reduced pressure and the residue purified by flash chromatography on silica gel with EtOAc:MeOH (95:5 to 90:10) to give the expected product (39) (2.10 g, 72%) together with unreacted starting material (490 mg). 1H NMR (d6 DMSO) δ 0.11 (s, 3H, CH3), 0.12 (s, 3H, CH3), 0.89 (s, 9H, 3CH3), 1.90 (ddd, J=13.2, 7.7 and 5.7 Hz, 1H, 2.18 (ddd, J=13.2, 5.7 and 2.3 Hz, 1H, HH-2′), 3.72 (dd, J=11.5, 3.6 Hz, 1H, HH-5′), 3.80 (dd, J=11.5, 2.8 Hz, 1H, HH-5′), 3.86-3.89 (m, 1H, H-4′), 4.14-4.18 (m, 1H, H-3′), 5.22 (1H, d, J=4.1 Hz, OH), 6.09 (1H, dd, J=7.8, 5.8 Hz, H-1′), 6.60 (br s, 1H, NHH), 7.81 (br s, 1H, NRH), 7.94 (s, 1H, H-6); MS (ES): m/z (%) (M+H) 468 (90%).

Source