Sodium Methoxide → (2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3-methoxy-4-methylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (56) (200 mg, 0.320 mmole) in NaOMe (25 wt % in MeOH, 10 mL, 43.2 mmole) were added cupric oxide (25.5 mg, 0.320 mmole) and KI (53.1 mg, 0.320 mmole). The resulting solution was stirred at 120° C. overnight. The reaction mixture was filtered through Celite® bed and concentrated in vacuo. The crude residue was purified on reverse phase preparative HPLC to yield the title compound 59 (24.3 mg, 0.0595 mmole, 19%) as a yellow solid.

Provenance & Evidence