Methanol → 1,6-Anhydro-4-O-benzyl-3-deoxy-beta-D-erythro-hexopyranos-2-ulose dimethyl acetal

Participants

Reaction Steps

1,6-Anhydro-4-O-benzyl-3-deoxy-β-D-erythro-hexopyranos-2-ulose (Example 6) (0.30 g) was dissolved in 3% HCl in dry methanol (10 ml) and the solution allowed to stand at room temperature for 0.5 h. Chloroform was added and the solution was washed with saturated aqueous sodium hydrogen carbonate, water, dried (MgSO4), and concentrated to a syrup. Purification by flash chromatography on silica gel gave the title compound (0.29 g) [α]D -52.1°; 13C-nmr data: 99.6 (C-1), 96.8 (C-2), 29.0 (C-3), 72.6 (C-4), 74.6 (C-5), 65.9 (C-6), 70.6 (PhCH2O), 138.1, 128.5, 127.7 and 127.6 (aromatic), 49.1 and 47.9 (OCH3).

Provenance & Evidence