반응 #1994286

반응 방정식

tetrabutylammonium fluoride

nucleoside

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

→

product ( 41 )

3′-O-Allyl-5-iodo-2′-deoxycytidine

용매

THF

THF

반응 조건

후처리

1. 1
   기타quenched by addition of H2O (5 ml)
2. 2
   기타THF was evaporated
3. 3
   추출aqueous residue extracted into EtOAc (3×25 ml)
4. 4
   건조Combined organic extracts were dried (MgSO4)
5. 5
   여과filtered
6. 6
   기타the volatiles evaporated under reduced pressure
7. 7
   기타giving a crude material which
8. 8
   기타was purified by flash chromatography on a pre-packed silica column
9. 9
   세척eluted with EtOAc

실험 절차

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%).

출처