Benzyl Alcohol → Benzyl beta-D-ribofuranoside

Participants

Reaction Steps

Benzyl alcohol (2.07 mL, 20 mmol) was added to a solution of β-D-ribofuranose-1,2,3,5-tetraacetate (3.18 g, 10 mmol) and zinc bromide (2.25 g, 10 mmol) in toluene (31.8 mL), and the mixture was stirred at ambient temperature for 20 hours. To the resulting solution was added aqueous saturated sodium hydrogen carbonate solution (31.8 mL), for layer separation. To the resulting aqueous layer was added toluene (31.8 mL) for extraction. The resulting two organic layers were combined together, washed with aqueous saturated sodium chloride solution (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the resulting oily 1-O-benzyl-β-D-ribofuranose-2,3,5-triacetate were added methanol (31.8 mL) and a solution of 28% sodium methoxide in methanol (0.2 mL, 1 mmol), the mixture was stirred at ambient temperature for 2 hours, and the resulting mixture was concentrated under reduced pressure. The resulting oily matter was purified by silica gel column chromatography, to recover the desired 1-O-benzyl-β-D-ribofuranose (2.24 g; yield of 93.2%) as a white solid. Melting point: 95° C.

Provenance & Evidence