Hydrochloric Acid → (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

Participants

Reaction Steps

To the above-obtained toluene solution of methyl 1-C-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-α-glucopyranoside were added pyridine (7.39 g) and 4-dimethylaminopyridine (19 mg). Thereto was added acetic anhydride (7.94 g) at 1.7 to 3.3° C., followed by stirring at room temperature for 12 hours. To the reaction mixture was added hydrochloric acid (2 M, 50 ml), followed by extraction. The organic layer was washed with a 5% aqueous sodium hydrogencarbonate solution (75 ml) and successively with an aqueous sodium chloride solution (25%, 50 ml), and subjected to vacuum distillation to distil off the solvent until the residue became 15 ml, to obtain, as a toluene solution, methyl 2,3,4,6-tetra-O-acetyl-1-C-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-α-glucopyranoside.

Provenance & Evidence