Hydrochloric Acid → (1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-Dioxabicyclo [3.2.1]Octane

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Reaction Steps

To a stirred solution of nucleoside 17 (0.63 g, 0.81 mmol) in a mixture of ethanol and H2O (40 cm3, 1:1, v/v) at room temperature was added an aqueous solution of sodium hydroxide (1M, 7 cm3). The resulting mixture was heated under reflux for 16 h and then neutralised by addition of dilute hydrochloric acid (10 cm3). The volume of the mixture was reduced to 50% and extraction was performed using dichloromethane (50 cm3×3). The combined organic phase was dried (Na 2SO4) and evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (99:1,v/v) as eluent to give nucleoside 18 as a white solid material (0.40 g, 93%) after evaporation of the solvents under reduced pressure.

Provenance & Evidence