alpha-D-Glucopyranosyl bromide, tetraacetate → 2,3,4,6-Tetra-O-acetylglucopyranosylisothiocyanate

Participants

Reaction Steps

Potassium thiocyanate (2.81 g, 28.7 mmol), tetrabutylammonium hydrogen sulphate (1.22 g, 3.59 mmol) and molecular sieves (6.00 g) were stirred in absolute acetonitrile (500 ml) for 30 minutes. 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 37 (5.90 g, 14.4 mmol) was then dissolved in acetonitrile, added to the reaction flask and refluxed for 90 minutes. The solution was then allowed to cool, filtered through a celite pad and concentrated. Purification by column chromatography in hexane:ethyl acetate 2:1 (v/v) to give 52 (4.26 g, 76%).

Provenance & Evidence