4-Toluenesulfonyl chloride → HCID 14214839, compound

Participants

Reaction Steps

D-Glucose (20.0 g, 0.111 mol) was placed in a 1000-mL round-bottomed flask, and pyridine (300 ml) was added. Some of glucose remained undissolved. p-Toluensulfonyl chloride (22.0 g, 0.115 mol) was added at ambient temperature. After stirring for 11 h, acetic anhydride (80 ml, 0.83 mol) was added in one portion. Gentle exothermic reaction took place. After being stirred for 1.5 h, the mixture was evaporated. Ethanol (200 ml) was added to a residual oil. The oil was dissolved and soon a white crystal appeared. After the mixture stood undisturbed at −10° C. for 27 h, the crystal was collected on a glass filter, washed with cold ethanol (25 ml, twice), and dried under reduced pressure. 6-O-(p-Toluenesulfonyl)-1,2,3,4-tetra-O-acetyl-β-D-glucose (compound 5) was obtained in 33% yield (18.5 g, 36.8 mmol).

Provenance & Evidence