Tetrahydrofuran → Ceramide NG

Participants

Reaction Conditions

Reaction Steps

A THF suspension (2 mL) containing sodium borohydride (39.2 mg, 0.96 mmol) was heated to 60° C., and ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (300.0 mg, 0.49 mmol) synthesized in the same manner as Example 17 was added for 2.5 hours. After completion of the dropwise addition, the mixture was further stirred at 60° C. for 24 hours. After ethyl acetate and water were added thereto, the reaction mixture was stirred at 60° C. for 1 hour. After the organic layer was separated, the obtained organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was removed in reduced pressure. It was confirmed that 219.4 mg of the title compound was contained (yield: 78%). HPLC analysis was carried out to find that anti-form:syn-form was 81:19 and the optical purity of the anti-form was 99% ee.

Provenance & Evidence