Tetrabutylammonium Fluoride → 1-(5-O-Acetyl-2-deoxy-4-ethynyl-beta-D-threo-pentofuranosyl)-thymine

Participants

Reaction Steps

To a THF (4 mL) solution of 11 (169.7 mg, 0.402 mmol) was added tetrabutylammonium fluoride (1M in THF, 602 μL, 0.602 mmol) under Ar atmosphere. After being stirred for 1 h at room temperature, the solvent was evaporated. Silica gel column chromatography (CHCl3/MeOH=100/1) of the residue gave 12 (114.7 mg, 93%) as a foam: UV (MeOH) λmax 265 nm (ε8400), λmin 233 nm (ε1700); 1H NMR (CDCl3 after addition of D2O) δ1.93 (3H, d, J6,Me=1.3 Hz, Me), 2.14-2.18 (1H, m, H-2′a), 2.18 (3H, s, Ac), 2.59 (1H, s, ethynyl), 2.94-3.02 (1H, m, H-2′b), 4.22 (1H, d, Jgem=11.4 Hz, H-5′a), 4.31 (1H, d, J2′b,3′=5.5 Hz, H-3′), 4.68 (1H, d, Jgem=11.4 Hz, H-5′b), 6.24 (1H, dd, J1′,2′a=2.9 Hz and J1′,2′b=9.0 Hz, H-1′), 7.60 (1H, d, J6,Me=1.3 Hz, H-6); 13C NMR (CDCl3) δ12.52, 20.84, 38.76, 63.30, 74.73, 76.23, 79.85, 82.08, 85.33, 111.41, 137.93, 150.53, 163.63, 171.98; FAB-HR-MS m/z calcd for C14H17N2O6 309.1087 (M++H). Found 309.1074.

Provenance & Evidence