Sodium Thiosulfate → (3aR,4R,6R,6aR)-6-(6-Chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-carbaldehyde

Participants

Reaction Steps

To a suspension of Dess-Martin periodinane (16.42 g, 0.03872 mol) in anhydrous methylene chloride (88.0 mL) cooled in an ice/water bath was added [(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol (11.50 g, 0.03520 mol) in methylene chloride (200 mL). The reaction was stirred under an atmosphere of nitrogen and allowed to warm to ambient temperature. After 2 hours, a further portion of Dess-Martin periodinane (1.00 g, 0.00236 mol) was added. After 3 hours, a solution (200 mL) of sodium thiosulfate (50 g in 200 mL of saturated aqueous sodium bicarbonate) was added and the mixture stirred for 10 min. The aqueous was extracted 2×250 mL methylene chloride and 8×50 mL of chloroform. The combined organics were washed with water and dried over magnesium sulfate and concentrated in vacuo to dryness. The residue was taken up in dry toluene (200 mL) and concentrated in vacuo, and then taken up in dry methylene chloride and concentrated in vacuo to yield the product as a foam (9.83 g, 86%).

Provenance & Evidence