Tetrahydrofuran → 1-O-methyl 2,3-dibenzoyl-beta-D-ribofuranoside

Participants

Reaction Steps

A solution of 1-O-methyl 5-(t-butyldiphenylsilyl)-2,3-dibenzoyl-β-D-ribofuranoside (849 mg, 1.39 mmol) and 1.0M tetrabutylammonium fluoride in THF (1.53 ml, 1.53 mmol) was stirred for 2 h at room temperature. After evaporation of the solvent, the residue was purified by silica gel column chromatography (Hx-EtOAc, 1:1) to yield 1-O-methyl 2,3-dibenzoyl-β-D-ribofuranoside [Rf =0.50 (Hx-EtOAc, 1:1), 461 mg, 89%] as thick syrup. 1H NMR (DMSO-d6) d 3.38 (s, 3H, --OCH3), 3.62 (m, 2H, H-5), 4.37 (q, J=5.2 Hz, 1H, H-4), 5.02 (pseudo t, J=6.0 and 5.3 Hz, 1H, exchangeable with D2O, 5-OH), 5.18 (s, 1H, H-1), 5.45 (m, 1H, H-2), 5.53 (t, J=5.2 Hz, 1H, H-3), 7.42-7.88 (m, 10H, Ar). Anal. Calcd for C20 H20O7 : C, 64.51; H, 5.41; Found: C, 64.37; H, 5.47.

Provenance & Evidence