4-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside → 4-aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside

Participants

Reaction Steps

To 91.3 g of 4-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside suspended in 100 ml of acetic acid was added 10 g of 10% palladium-on-charcoal catalyst in a Parr hydrogenation bottle, and this was hydrogenated on a Parr hydrogenator for 12 hours. The catalyst was filtered from the solution through diatomaceous earth and washed thoroughly with methanol. The solvents were evaporated in vacuo. The residue was dissolved into one liter of toluene and again evaporated. The residue was dissolved in methylene chloride and passed through a pad of magnesium silicate and the volume of the solution was adjusted to about 300 ml. To this was added 1.5 liters of ether and 5 g of activated charcoal, the solution was boiled for 3 minutes, the charcoal was filtered off and the solvents were again evaporated. The yellow foam was crystallized from 1.5 liters of ether to yield 69.6 g of the desired compound as light yellow crystals, isolated in three crops, m.p. 145°-148° C.

Provenance & Evidence