99043-04-6Relevant articles and documents
Effective synthesis of 1β-acyl glucuronides by selective acylation
Perrie, Jennifer A.,Harding, John R.,Holt, David W.,Johnston, Atholl,Meath, Paul,Stachulski, Andrew V.
, p. 2591 - 2594 (2005)
(Chemical Equation Presented) Acyl glucuronides are vital metabolites for many carboxylic acid containing drugs. We report an efficient new method for the chemical synthesis of these molecules by selective 1β-acylation of allyl glucuronate with carboxylic
Efficient synthesis of 1β-O-acyl glucuronides via selective acylation of allyl or benzyl d-glucuronate
Bowkett, Elizabeth R.,Harding, John R.,Maggs, James L.,Park, B. Kevin,Perrie, Jennifer A.,Stachulski, Andrew V.
, p. 7596 - 7605 (2008/02/08)
Acyl glucuronides are key metabolites for many carboxylic acid-containing drugs, notably those of the non-steroidal anti-inflammatory class. In the processes of drug safety assessment and new drug development, it is essential that acyl glucuronides, if formed in vivo, should be made conveniently available for bioevaluation. We recently showed that selective acylation of allyl glucuronate is a promising method for the synthesis of these metabolites in good yield and with excellent β-anomeric selectivity. We now give fuller details of the allyl ester method and further report that benzyl glucuronate performs at least equally well in the acylation step, offering the advantage of very mild deprotection by catalytic transfer (or conventional) hydrogenation. Depending on the compatibility of other functional groups, as discussed below, this will be the method of choice for many acyl glucuronide syntheses. The value of the method is demonstrated in particular by the synthesis of several acyl glucuronides that are known metabolites of important drugs.
