2,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide → 6-acetyl-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Participants

Reaction Steps

1.29 g (9.47 mM) of zinc chloride are melted and left to cool to room temperature. 4 g of 13× molecular sieve, 50 ml of acetonitrile, 3.1 g (8.7 mM) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1.4 g (8 mM) of silver imidazolate and 1 g (7.3 mM) of 6-acetyl-3-pyridinol are added. The mixture is stirred for 3 hours at 65° C. After filtration, the material on the filter is rinsed with ethyl acetate and the volatile solvents are evaporated off under reduced pressure. The product is purified by chromatography on silica gel using a toluene/isopropanol mixture (98/2; v/v) as the eluent. The purified product is crystallized from isopropyl alcohol to give the expected product in the form of a white solid with a yield of 15%.

Provenance & Evidence