Réaction #1994286

Équation de réaction

tetrabutylammonium fluoride

nucleoside

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

→

product ( 41 )

3′-O-Allyl-5-iodo-2′-deoxycytidine

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Autrequenched by addition of H2O (5 ml)
2. 2
   AutreTHF was evaporated
3. 3
   Extractionaqueous residue extracted into EtOAc (3×25 ml)
4. 4
   SéchageCombined organic extracts were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Autrethe volatiles evaporated under reduced pressure
7. 7
   Autregiving a crude material which
8. 8
   Autrewas purified by flash chromatography on a pre-packed silica column
9. 9
   Lavageeluted with EtOAc

Mode opératoire

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%).

Source