(Diethylamino)sulfur trifluoride → HCID 67982275, compound

Participants

Reaction Steps

To a solution of (-(3aR,5R,6S,7R,7aR)-6-(benzoyloxy)-2-((tert-butoxycarbonyl)(ethyl)amino)-7-hydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)methyl benzoate (0.49 g, 0.88 mmol) in anhydrous DCM (3 mL), at −40° C. under N2, was added DAST (1.0 g, 6.2 mmol). After addition the mixture was stirred at room temperature overnight. After the reaction mixture was again cooled at −40° C., it was diluted with DCM (20 mL), and then quenched by adding satd. aqueous NaHCO3 dropwise. The organic layer was collected, and the aqueous was extracted with DCM (2×15 mL). The combined extract was dried over anhydrous Na2SO4. After filtration the solvent was evaporated under reduced pressure, and the residue was purified on silica gel by flash column chromatography (EtOAc/hexanes, 1:5 to 2:7), affording (-(3aR,5R,6R,7R,7aR)-6-(benzoyloxy)-2-((tert-butoxycarbonyl)(ethyl)amino)-7-fluoro-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)methyl benzoate as a white solid (0.14 g, impure, ˜28%).

Provenance & Evidence