Reaktion #164142

Reaktionsgleichung

4

5′-O-tert-butyldimethylsilyloxy-(5-(4-(N-trifluoroacetyl-2-aminoethoxy)but-2-yn-1-yl))-2′,3′-dideoxyuridine

tetrabutylammonium fluoride

→

product 5

Ausbeute 43.5%

5-(4-(N-trifluoroacetyl-2-aminoethoxy)but-2-yn-1-yl)-2′,3′-dideoxyuridine

Ausbeute 43.5%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter evaporating solvent
2. 2
   Sonstigethe organic residue was purified by silica gel column chromatography with MeOH/CH2Cl2

Vorschrift

To a solution of 4 (90.0 mg, 0.17 mmol) in THF (5 mL) was added 1.0 M tetrabutylammonium fluoride (TBAF, 0.2 mL, 0.19 mmol), which was stirred at r.t. for 3 h. After evaporating solvent, the organic residue was purified by silica gel column chromatography with MeOH/CH2Cl2 to give the product 5 (30 mg, 0.074 mmol, 43%). 1H NMR (CDCl3, 300 MHz) δ 8.01 (t, 1H, H6, J=1.2 Hz), 6.08 (dd, 1H, H1′, J=3.6 and 6.6 Hz), 4.23 (t, 2H, CH2), 4.20-4.10 (m, 1H, H4′), 3.85 (dd, 1H, H5′, J=3.3 and 11.4 Hz), 3.75-3.63 (m, 3H, H5′, CH2), 3.50-3.45 (m, 2H, CH2), 3.30-3.25 (m, 2H, CH2), 2.47-2.34 (m, 1H, H2′), 2.15-1.80 (m, 3H, H2′, 2 H3′). 19F NMR (CDCl3, 282.2 MHz) δ −77.79 (s, CF3).

Quelle