(9H-Fluoren-9-yl)methyl 2-oxoethylcarbamate

105496-31-9

156939-62-7

General procedure for the synthesis of N-fluorenylmethoxycarbonylglyceraldehyde from 2-(N-fluorenylmethoxycarbonylamino)ethanol: Diisopropylethylamine (12.4 mL, 70.6 mmol) was added to a dichloromethane (50 mL) suspension of 2-(N-fluorenylmethoxycarbonylamino)ethanol (5.0 g, 18 mmol). The reaction mixture was cooled to -40 °C and a solution of sulfur trioxide pyridine complex (11.2 g, 70.6 mmol) in dimethyl sulfoxide (49.5 mL) was added dropwise over 15 min. After continuous stirring at -40 °C for 1 h, the reaction was quenched with a mixture of ice water and saturated saline. The organic solvent was removed by concentration under reduced pressure, and the resulting off-white precipitate was collected by filtration and dried under vacuum. Finally, purification was carried out by silica gel fast column chromatography to afford N-fluorenylmethoxycarbonylglyceraldehyde (4.7 g, 94% yield) using ethyl acetate/hexane (1:1, v/v) as eluent.