Sodium Hydroxide → (1R,3R,4S,7R)-1-(Hydroxymethyl)-7-benzyloxy-3-(thymin-1-yl)-2,5-dioxabicyclo-[2.2.1]heptane

Participants

Reaction Conditions

Reaction Steps

To a solution of nucleoside 11 (329 mg, 0.54 mmol) in ethanol/water (10 cm3, 1:1, v/v) was added 6M NaOH (aq) (0.9 ml, 5.4 mmol). The mixture was refluxed at 80° C. for 43 h followed by evaporation to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (2.4% methanol, v/v) as eluent to afford nucleoside 12 (85 mg, 44%). δC ((CD3)2SO) 163.8, 150.3, 138.0, 135.8, 128.3, 127.7, 127.5, 108.0, 90.2, 86.5, 86.4, 79.3, 76.5, 72.5, 71.2, 57.2, 40.2, 40.0, 39.8. 39.6, 39.4, 39.2, 39.0, 12.3.

Provenance & Evidence