1772-03-8

White Crystalline Solid

Specifically inhibits COX-2 by preventing COX-2 N-glycosylation and by increasing COX-2 protein turnover in a proteasome-dependent manner.

Galactosamine (D-GalN) is synthesized from galactose and is potential hepatotoxic agent. D-GalN in combination with lipopolysaccharide leads to the development of lethal liver injury and hepatic failure. It sensitizes cells to the toxic effects of the cytokine in particular the tumor necrosis factor(TNF).

A preparation process of D-galactosamine hydrochloride, adding 500ml absolute ethanol into a 1000ml three-necked flask with a reflux condenser, a stirrer and a thermometer, stirring at room temperature and adding 100g of dimethyl dodecyl respectively Tetradecylamine and 500g of solid-supported silica were heated to 110°C within 30 minutes, kept in reflux for 5 hours and then lowered to 29°C, filtered and dried to obtain 589g of organic amine solid-supported catalyst. In a 1000ml three-necked flask with a stirrer and a thermometer, 190g of 5-methyltryptamine hydrochloride and 600ml of dimethylamide were respectively added, 59g of organic amine solid-supported catalyst and 150g of chloropropene were added, and the reaction was carried out for eight hours at room temperature. Liquid filtration, the obtained filtrate was evaporated to dryness and dissolved in 1150ml of isopropanol, and 89ml of 36wt% hydrochloric acid was added to hydrochloride to obtain 130.32g of white crystals of 2-amino-2-deoxy-D-galactose hydrochloride with a yield of 42.05%.

Dissolve the hydrochloride in a small volume of H2O. Then add three volumes of EtOH, followed by acetone until faintly turbid and keep overnight in a refrigerator. [Roseman & Ludoweig J Am Chem Soc 76 301 1954, Beilstein 4 IV 2024.]