تفاعل #1994286

معادلة التفاعل

tetrabutylammonium fluoride

nucleoside

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

→

product ( 41 )

3′-O-Allyl-5-iodo-2′-deoxycytidine

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىquenched by addition of H2O (5 ml)
2. 2
   أخرىTHF was evaporated
3. 3
   استخلاصaqueous residue extracted into EtOAc (3×25 ml)
4. 4
   تجفيفCombined organic extracts were dried (MgSO4)
5. 5
   ترشيحfiltered
6. 6
   أخرىthe volatiles evaporated under reduced pressure
7. 7
   أخرىgiving a crude material which
8. 8
   أخرىwas purified by flash chromatography on a pre-packed silica column
9. 9
   غسيلeluted with EtOAc

الإجراء التجريبي

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%).

المصدر