Hydrochloric Acid → 2-[1-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]amino]ethylidene]-5,5-dimethylcyclohexane-1,3-dione

Participants

Reaction Steps

A solution of Benzyl 2-Acetamido-2-deoxy-α-D-glucopyranoside (4.70 g, 15.11 mmol) in 1 M NaOH solution was refluxed at 120° C. for 15 h. The reaction mixture was cooled to room temperature, neutralised with 1 M HCl solution and concentrated. The residue was dissolved in dry ETOH (50 ml) and filtered. 2-Acetyldimedone (4.11 g, 22.6 mmol) and N,N-diisopropylethylamine (2 ml) were added to the filtrate, and the mixture was refluxed for 2 h. The reaction mixture was evaporated to dryness, and the residue was taken up in EtOAc (50 ml), washed with 1M KHSO4 solution, brine, and evaporated to give Benzyl 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-α-D-glucopyranoside (7) (3.78 g, 58%).

Provenance & Evidence