(Diethylamino)sulfur trifluoride → (2,3,4-tri-O-acetyl)-L-fucopyranosyl fluoride

Participants

Reaction Steps

(2,3,4-Tri-O-acetyl)-L-fucopyranose (13.1 g) is dissolved in methylene chloride (100 ml), and thereto is added with stirring DAST (10.9 g) under ice-cooling, and the mixture is stirred for 4 hours under ice-cooling. The reaction mixture is poured into ice-water (200 g), and the mixture is separated. The organic layer is dried, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (n-hexane:ethyl acetate=1:4→1:2) to give (2,3,4-tri-O-acetyl)-L-fucopyranosyl fluoride (10.6 g) in the form of a mixture of α-anomer and β-anomer.

Provenance & Evidence