Reacción #1994286

Ecuación de reacción

tetrabutylammonium fluoride

nucleoside

3′-O-Allyl-5′-O-(tert-butyldimethylsilyl)-5-iodo-2′-deoxycytidine

→

product ( 41 )

3′-O-Allyl-5-iodo-2′-deoxycytidine

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched by addition of H2O (5 ml)
2. 2
   OtroTHF was evaporated
3. 3
   Extracciónaqueous residue extracted into EtOAc (3×25 ml)
4. 4
   SecadoCombined organic extracts were dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Otrothe volatiles evaporated under reduced pressure
7. 7
   Otrogiving a crude material which
8. 8
   Otrowas purified by flash chromatography on a pre-packed silica column
9. 9
   Lavadoeluted with EtOAc

Procedimiento

To a solution of the starting nucleoside (40) (323 mg, 0.64 mmol) in THF (15 ml) under N2 protected atmosphere was added at room temperature tetrabutylammonium fluoride (TBAF) 1M in THF (0.7 ml, 0.7 mmol). Mixture stirred for one hour and then quenched by addition of H2O (5 ml). THF was evaporated and aqueous residue extracted into EtOAc (3×25 ml). Combined organic extracts were dried (MgSO4), filtered and the volatiles evaporated under reduced pressure giving a crude material which was purified by flash chromatography on a pre-packed silica column eluted with EtOAc. The product (41) was obtained as a white solid (233 mg, 93%). 1H NMR (d6 DMSO) δ 1.96-2.05 (m, 1H, H-2′) 2.24 (ddd, J=13.5, 5.8 and 2.8 Hz, 1H, H-2′), 3.50-3.62 (m, 2H, H5′), 3.91-3.97 (m, 2H, H3′, H4′), 4.03-4.07 (m, 2H, HHC—CH═), 5.11-5.16 (m, 2H, OH, CH═CHH), 5.24 (dd, J=17.2, 1.6 Hz, 1H, CH═CHH), 5.82-5.91 (m, 1H, CH═CHH), 6.02 (dd, J=7.6, 6.0 Hz, 1H, H-1′), 6.60 (s, 1H, NHH), 7.79 (s, 1H, NHH), 8.21 (s, 1H, H-6). MS (ES): m/z (%) (M−H) 392 (100%).

Fuente