HCID 123292264, compound → HCID 123928181, compound

Participants

Reaction Steps

To a solution of tert-butyl ((3aR,5R,6S,7aR)-6-(benzyloxy)-5-(1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.406 g, 0.961 mmol) in dry DCM (20 mL) was added DMP (0.615 g, 1.45 mmol). The reaction mixture was stirred at room temperature for 3 h, and then concentrated. The residue was diluted with saturated aqueous NaHCO3 solution (20 mL) and 1 M Na2S2O3 aqueous solution (5 mL), and extracted with EtOAc (2×20 mL). The combined extract was dried over Na2SO4. After filtration the solvent was evaporated under reduced pressure, and the residue was purified on silica gel by automatic flash column chromatography (EtOAc/hexanes, 1:4 to 2:3), affording tert-butyl ((3aR,5S,6S,7aR)-5-acetyl-6-(benzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.32 g), which was impure and used in the next step without further purification.

Provenance & Evidence