21085-72-3

The specific preparation steps are as follows: Methyl 1,2,3,4-tetra-O-acetyl-D-glucuronide (3) (15.0 g, 4 mmol) was added to an acetic acid solution of hydrogen bromide (hydrogen bromide mass percentage 33%) (60 mL) and kept stable at no more than 10 °C. Then, the mixture was naturally heated to room temperature and stirred for 2 hours. The reaction was concentrated to dryness and dissolved in 100 mL of ethyl acetate. The organic phase was then washed three times with an aqueous sodium bicarbonate solution and dried with anhydrous sodium sulfate. The filtrate was concentrated to dryness and 50 mL of petroleum ether was added to precipitate a solid. The solid was filtered to obtain ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER (4) (yield 14.3 g, 90%).

Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of HMR1098-S-glucuronide methyl ester, a new K-ATP-blocking agent being developed as a drug for prevention of sudden cardiac death.
Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of water-soluble glucuronide derivatives of Camptothecin, which is used for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT).
Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of glucuronide prodrug compounds of Janus kinase (JAK) inhibitor tofacitinib, which could be cleaved by β-glucuronidase enzymes such as those produced by the microbiome in the gastrointestinal tract, thereby increasing levels of tofacitinib at the site of gastrointestinal inflammation and limiting the systemic exposure of tofacitinib when treating localized inflammatory diseases.