D-(-)-Fructose → HCID 11677410, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 55 (40 mg, 0.0857 mmol) in 1.3 mL CH3CN/DMM—1/1 at rt were added successively 0.8 mL of a buffer solution (Na2B4O7.10 H2O [0.05M] in Na2EDTA [4.10−4M]), BU4N(HSO4) (1.2 mg, 0.003 mmol) and fructose-derived ketone (17.7 mg, 0.0685 mmol). The reaction mixture is cooled to 0° C. and were added separately, in a same time over 1 h30, Oxone® (73.8 mg, 0.120 mmol) in 1 mL Na2EDTA and K2CO3 (68.7 mg, 0.497 mmol) in 1 mL H2O. The solution is stirred 3 h 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 of crude product by prep-HPLC afforded 56, 50% conversion in a 8/1 ratio.

Provenance & Evidence