A New Synthetic Route to 4-Methylumbelliferyl-β-d-glucopyranosiduronic Acid (MUG)

Autor:	Yulianela Ibarra Reyes, Alexander Balbuzano-Deus, Juan C. Rodríguez-Domínguez, Anais Fernández Villalobo, Gilbert Kirsch, Miriam Mesa Hernández, Miguel A. López-López
Rok vydání:	2007
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Acetylation Sodium hypochlorite Carboxylic acid Yield (chemistry) Organic Chemistry Organic chemistry Methanol Methoxide Benzene Catalysis
Zdroj:	Synlett. 2007:0649-0651
ISSN:	1437-2096 0936-5214
Popis:	A synthetic route to prepare 4-methylumbelliferyl-β-D-glucopyranosiduronic acid (MUG) from 4-methylumbelliferyl-β-D-glucopyranoside (MUGluc) was developed. The primary hydroxyl group in MUGluc was protected by tritylation followed by acetylation of secondary hydroxyls. The triphenylmethyl group was selectively removed by treatment with iodine-methanol in benzene and the free hydroxyl was transformed into the carboxylic acid by phase-transfer oxidation with sodium hypochlorite and TEMPO as catalyst. Finally, the acetate groups were removed by reaction with barium methoxide in methanol to afford the MUG with an overall yield of 37% from the MUGluc.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::def870d3c76802d60244780b95c7e40f https://doi.org/10.1055/s-2007-967972 Zobrazit plný text záznamu