(Diethylamino)sulfur trifluoride → Benzyl 2-O-chloroacetyl-4-deoxy-4-fluoro-3,6-di-O-pivaloyl-beta-D-glucopyranoside

Participants

Reaction Conditions

Reaction Steps

Compound (19) (300 mg, 0.583 mmol) was dissolved in dichloromethane (5.8 ml), and diethylaminosulfatrifluoride (DAST) was added to the solution with stirring under an argon stream at −15° C. The mixture was returned to room temperature 10 minutes after the addition of DAST and reacted for 1 hour. Disappearance of the material was confirmed by TLC, the DAST was quenched with methanol (3 ml), and the reaction mixture was concentrated in a vacuum. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:6), giving Compound (20) (in an amount of 211 mg, yield 70%).

Provenance & Evidence