Hydrochloric Acid → HCID 52914480, compound

Participants

Reaction Steps

To the above crude mixture of (3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran (˜100 mg, 0.14 mmole) in methanol (3 mL), 10% Pd/C (100 mg) and 2 drops of con. HCl added and stirred under hydrogen atmosphere at room temperature for 18 hours. The reaction mixture was filtered through cetlie bed, washed with methanol (20 mL). The crude product was purified by preparative chiral HPLC to furnish 10 mg of (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-triol (Ex. 11) and 20 mg of (5S,6R,7R,8S)-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol (Ex. 2).

Provenance & Evidence