Pyridine → HCID 86696314, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diacetone-D-glucose (1.56 g, 6 mmol) and pyridine (1.09 g, 1.12 mL, 13.8 mmol) in methylene chloride (6 mL) at −78° C. was added slowly a solution of 1-chloroethyl chloroformate (970 mg, 732 μl, 6.78 mmol) in methylene chloride (4 mL). After addition, the reaction mixture was allowed to stir at −78° C. for 1.5 h. Then the cold bath was removed and the reaction mixture was warmed up to room temperature. The reaction mixture was concentrated in vacuo and taken up in diethyl ether. The precipitate was filtered and the solid was washed thoroughly with diethyl ether. The filtrate and washing solutions were combined and concentrated to give 2.135 g of 1-chloroethyl (3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-yl carbonate as clear light yellow thick oil, which was used directly without further purification.

Provenance & Evidence