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Typical experimental procedure from saccharides acetates: A solution of d-ribose pentaacetate (0.49 g, 1.5 mmol) and HBr (33% solution in acetic acid, 1.5 mL) in dry chloroform (10 mL) was stirred under nitrogen for about 4 h at room temperature until the completion of the reaction monitored by TLC. After the volatiles were removed, the following reagents were added in order of: chloroform (10 mL), saturated sodium bicarbonate solution (5 mL), sodium azide (0.14 g, 2.2 mmol), tetrabutylammonium hydrogen sulfate (0.5 g, 1.5 mmol), phenyl acetylene (0.15 g, 1.5 mmol), copper sulfate pentahydrate (12 mg, 0.05 mmol), sodium ascorbate (30 mg, 0.15 mmol), and ethanol (5 mL). The reaction mixture was stirred at room temperature for about 16 h. Solvents were removed and the residue was cooled in ice water bath. The precipitate was collected by filtration and washed with 0.1 M ammonium hydroxide (10 mL) to afford the product 10 in 81% yield. The aqueous layer could be further extracted with chloroform to recover more products
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