Acetic Acid → HCID 69663726, compound

Participants

Reaction Conditions

Reaction Steps

Concentrated sulfuric acid (97%, 99 mL) was added to a solution of 2,3,5-tri-O-benzoyl-1-O-methyl-4-C-methyl-β-D-ribofuranose (1.8 g, 3.6 mmoles) in a mixture of acetic acid (9.0 mL) and acetic anhydride (0.90 mL) at 0° C. The reaction mixture was stirred at 25° C. for 16 h and diluted with ethyl acetate (50 mL) and brine (10 mL). The organic extract was washed with brine (3 times), with a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate, filtered, and the filtrate was evaporated to dryness. The residue was dissolved with a mixture of ethyl acetate and hexanes (1:4, v/v) and the b anomer of the title compound crystallized instantaneously. The white crystals were filtered to give 1.1 g (56%) of the title compound in its pure b anomer form. The filtrate was subjected to silica gel chromatography [ethyl acetate (20%) in hexanes] to give 0.6 g (32%) of the titled compound as an oil (3:1 mixture of a/b anomers).

Provenance & Evidence