Effective synthesis of 1beta-acyl glucuronides by selective acylation.
[reaction: see text] 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 1beta-acylation of allyl glucuronate with carboxylic acids catalyzed by HATU and then mild deprotection through treatment with Pd(PPh(3))(4) and morpholine. The method is effective for a range of aryl and alkyl carboxylic acids, including important drugs.
Perrie
Jennifer A
JA
The Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, UK.
Harding
John R
JR
Holt
David W
DW
Johnston
Atholl
A
Meath
Paul
P
Stachulski
Andrew V
AV
D000215:Acylation; D002264:Carboxylic Acids / Q000737:chemistry*; D020719:Glucuronides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D002264:Carboxylic Acids; D020719:Glucuronides; D009025:Morpholines; D009942:Organometallic Compounds; D010165:Palladium