Dichloromethane → di-tert-butyl (2R,3R)-2-(diethoxyphosphoryloxy)-3-hydroxysuccinate

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Reaction Steps

(Step 1) To di-tert-butyl tartrate (182 mg, 0.692 mmol), dichloromethane (1.73 mL), triethylamine (0.145 mL, 1.04 mmol), and diethylchlorophosphoric acid (0.050 mL, 0.346 mmol) were added, and the resulting mixture was stirred at room temperature for 20 hours. To the reaction mixture, water was added, and the resulting mixture was extracted with chloroform. The organic layer was dried, over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica, gel column chromatography (ethyl acetate/n-hexane=5/95 to 30/70), whereby di-tert-butyl (2R,3R)-2-(diethoxyphosphoryloxy)-3-hydroxysuccinate (46 mg, 33%) was obtained.

Provenance & Evidence