Boron tribromide → (2S,3R,4R,5S,6R)-2-(3-((5-(Furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-hydroxynaphthalen-1-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Participants

Reaction Steps

To a solution (2S,3R,4R,5S,6R)-2-(3-((5-(Furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-methoxynaphthalen-1-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol (compound 71b, 50 mg, 0.10 mmol) in CH2Cl2 (5 mL) at 0° C. was added boron tribromide (1.0 M in CH2Cl2, 0.52 mL, 0.52 mmol). The resulting mixture was stirred with gradual warming to ambient temperature over 2 h and re-cooled to 0° C. The mixture was quenched with MeOH and concentrated in vacuo. The resulting crude residue was purified by reverse phase preparative HPLC to yield the title compound (36 mg, 74%) as a white solid.

Provenance & Evidence