Réaction #1994271

Équation de réaction

imidazole

( 1 )

5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2′-deoxyuridine

t-butyldimethylsilylchloride

→

( 2 )

5′-O-(tert-butyidimethylsilyl)-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2′-deoxyuridine

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was quenched with sat. aq. NaCl solution
2. 2
   workup.ADDITIONEtOAc (25 ml) was added to the reaction mixture
3. 3
   Extractionthe aqueous layer was extracted with EtOAc three times
4. 4
   SéchageAfter drying the combined organics (MgSO4)
5. 5
   Autrethe solvent was removed under vacuum
6. 6
   AutrePurification by chromatography on silica (EtOAc:petroleum ether 8:2)

Mode opératoire

To a solution of (1) (656 mg, 1.74 mmol) in dry DMF (15 ml) was added t-butyldimethylsilylchloride (288 mg, 1.91 mmol) in small portions, followed by imidazole (130 mg, 1.91 mmol). The reaction was followed by TLC and was completed after stirring for 8 h at room temperature. The reaction was quenched with sat. aq. NaCl solution. EtOAc (25 ml) was added to the reaction mixture and the aqueous layer was extracted with EtOAc three times. After drying the combined organics (MgSO4), the solvent was removed under vacuum. Purification by chromatography on silica (EtOAc:petroleum ether 8:2) gave (2) as slightly yellow crystals (676 mg, 83%). 1H NMR (d6 DMSO) δ 0.00 (s, 6H, CH3), 0.79 (s, 9H, tBu), 1.93-2.00 (m, 1H, H-2′), 2.06-2.11 (m, 1H, H-2′), 3.63-3.75 (m, 2H, H-5′), 3.79-3.80 (m, 1H, H-4′), 4.12-4.14 (m, 3H, H-3′, CHO, 5.22 (d, J=4.1 Hz, 1H, OH), 6.03 (t, J=6.9 Hz, 1H, H-1′), 7.86 (s, 1H, H-6), 9.95 (t, J=5.4 Hz, 1H, NH), 11.61 (br s, 1H, NH). Mass (−ve electrospray) calcd for C20H28F3N3O6Si 491.17. Found 490.

Source