D-(-)-Fructose → HCID 86620184, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 48 (24 mg, 0.0495 mmol) in 0.75 mL CH3CN/DMM—1/1 at rt were added successively 0.46 mL of a buffer solution (Na2B4O7.10 H2O [0.05M] in Na2EDTA [4.10−4M]), Bu4N(HSO4) (0.67 mg, 0.0019 mmol) and fructose-derived ketone (10.2 mg, 0.0396 mmol). The reaction mixture is cooled to 0° C. and were added separately, in a same time over 1 h30, Oxone® (42.6 mg, 0.089 mmol) in 0.6 mL Na2EDTA and K2CO3 (39.7 mg, 0.287 mmol) in 0.6 mL H2O. The solution is stirred 1 h30 at 0° C. 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—50/45/5) afforded 49 in a 8/1 ratio as white crystals.

Provenance & Evidence