Acetic Acid → (2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Participants

Reaction Steps

To a solution of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (57) (125 mg, 0.223 mmole) in MeOH (5 mL) was added NaOMe (25 wt % in MeOH, 310 μL, 1.34 mmole). The reaction mixture was stirred at ambient temperature for 2 h before AcOH (2 mL) was added. Purification by reverse phase preparative HPLC provided the title compound 60 (24.8 mg, 0.0632 mmole, 28%) as a brown solid.

Provenance & Evidence