Dimethyl Sulfoxide → 1,2:5,6-Bis-O-(1-methylethylidene)-α-D-ribo-hexofuranos-3-ulose

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Reaction Steps

To a stirred solution of DMSO (10.65 mL, 150.1 mmol) in CH2Cl2 (300 mL) at -78° C under argon was added trifluoroaeetie arthydride (16.00 mL, 113.3 mmol) dropwise. The resulting white suspension was stirred at -78° C. for 10 min before a solution of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (20.0 g, 76.7 mmol) in CH2Cl2 (200 mL) was slowly added by cannula. The resulting mixture was stirred at -78° C. for 1 h before triethylamine (30.4 mL, 218 mmol) was slowly added and the reaction mixture allowed to warm to room temperature. Saturated aqueous NH4Cl (100 mL) was added and the organic phase was separated and washed with cold 1M aqueous HCl (2×100 mL), H2O (100 mL), saturated aqueous NaHCO3 (100 mL), H2O (100 mL), and saturated aqueous NaCl (100 mL). The organic phase was dried, filtered and concentrated to give the crude ketone (22.3 g) as a pale yellow oil. This material was used directly without further purification.

Provenance & Evidence