反応 #1994286

反応方程式

tetrabutylammonium fluoride

nucleoside

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

→

product ( 41 )

3′-O-Allyl-5-iodo-2′-deoxycytidine

溶媒

THF

THF

反応条件

後処理

1. 1
   その他quenched by addition of H2O (5 ml)
2. 2
   その他THF was evaporated
3. 3
   抽出aqueous residue extracted into EtOAc (3×25 ml)
4. 4
   乾燥Combined organic extracts were dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   その他the volatiles evaporated under reduced pressure
7. 7
   その他giving a crude material which
8. 8
   その他was purified by flash chromatography on a pre-packed silica column
9. 9
   洗浄eluted with EtOAc

実験手順

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%).

出典