Diisopropylethylamine → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-(3-fluoropropyl)thioureido)tetrahydro-2H-pyran-2,4,5-triyl triacetate

Participants

Reaction Steps

To a solution of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanatotetrahydro-2H-pyran-2,4,5-triyl triacetate (0.850 g, 2.19 mmol) and 3-fluoropropylamine hydrochloride (0.251 g, 2.21 mmol) in DCM (10 mL), was added DIPEA (0.415 g, 4.00 mmol). The reaction mixture was stirred at room temperature for 30 min, and then concentrated under reduced pressure. The residue was purified on silica gel by flash column chromatography (EtOAc/hexanes, 2:1 in), affording (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-(3-fluoropropyl)thioureido)tetrahydro-2H-pyran-2,4,5-triyl triacetate as a white solid (0.91 g, 88%).

Provenance & Evidence