D-(-)-Fructose → HCID 11677457, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 37 (30 mg, 0.064 mmol) in 1 mL CH3CN/DMM—1/1 at rt were added successively 0.6 mL of a buffer solution (Na2B4O7.10 H2O [0.05M] in Na2EDTA [4.10−4M]), Bu4N(HSO4) (0.9 mg, 0.0025 mmol) and fructose-derived ketone (13.2 mg, 0.051 mmol). The reaction mixture is cooled to 0° C. and were added separately, in a same time over 1 h30, Oxone® (55.1 mg, 0.089 mmol) in 0.8 mL Na2EDTA and K2CO3 (51.3 mg, 0.371 mmol) in 0.8 mL H2O. The solution is stirred at 0° C. for 3 h and then is quenched with H2O, extracted 3 times with 10 mL AcOEt. The combined organic layers are dried (MgSO4) and concentrated in vacuum. Purification by flash column chromatography (Hexane/Acetone/MeOH—70/30/0 to 45/50/5) afforded 38, 76% conversion.

Provenance & Evidence