(2-{2-[2-((2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid benzyl ester → N-Acetyl-D-Galactosamine

Participants

Reaction Steps

The above prepared (2-{2-[2-((2R,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid benzyl ester (15.7 g, 25 mmol) was dissolved in 525 mL of ethyl acetate and hydrogenated over 1.6 g of Pd/C: (10%) under 1 atm. Of H2 at ambient temperature for 3 h. Filtration over Celite, evaporation of the solvent, followed by flash chromatography (SiO2, CH2Cl2/MeOH 80/20) gave 6.07 g of the title compound as a brownish gum MS (ISP): 536.5 [M−H]−.

Provenance & Evidence